Brock Lesnar’s Top Ten Greatest WWE Matches

Pure adrenaline, personified.

In 2002, the WWE introduced the world to one of the greatest pure athletes sport entertainment has ever seen. Size. Speed. Strength. Brock Lesnar was the total package and his abilities in the ring shocked and surprised as he went on to become the youngest WWE Champion ever at the age of 25 in his rookie year.

Since then, Brock Lesnar has become the only man in history to become the NCAA Division I, WWE, and UFC Heavyweight Champion. Fewer men have made a larger impact on the wrestling world despite having such a short stint in the industry. Lesnar’s original run with WWE only lasted from early 2002 until 2004. His last appearance was at WrestleMania XX.

Still in that time the Wisconsin native had some of the WWE’s greatest matches of the new millennium. No one made such an impact in just two short years, but in the beginning of 2004 Lesnar left the WWE.

After a short venture into professional football, Brock Lesnar set his sights on MMA. He remains the single most successful professional wrestler turned MMA fighter ever when he defeated Randy Couture to become the UFC Heavyweight Champion.

However, to the surprise of many, Lesnar retired from MMA in 2012 and after an eight year absence returned to the WWE the night after WrestleMania XXVIII. Since that day, Brock has been used strictly as a special attraction performer. Even though the number of matches he has had since he returned can be numbered on two hands, several of them still stand among his best.

Let’s see which feats of athletic prowess number among the “Beast Incarnates” best.



This was a match, on Rey Mysterio’s birthday, for Brock Lesnar’s WWE Championship.

Lesnar was in the middle of what would be his last reign as WWE Champion before leaving for almost a decade.

“The Next Big Thing” had many notably well received matches on WWE Smackdown! It really makes one realize just how vital Lesnar was to that show’s success during the 2002 and 2003 time period.

This match followed a simple, but effective, formula of playing-up Mysterio’s speed against Lesnar’s strength. Lesnar would use his power to man-handle Rey and in turn he would use his speed to wear out the WWE Champion and catch him off guard.

The  San Diego crowd was really into the match as it was one of Mysterio’s first opportunities being taken seriously in a main event setting.

Rey Mysterio’s speed was not enough to wear out the well-conditioned champion. Lesnar retained his title via submission.

Also considered:

  • Brock Lesnar vs. Hulk Hogan (Smackdown!; August 2002): How many people can you name who have defeated “The Immortal” Hulk Hogan without the aid of some sort of dusty finish? This match makes the honorable mention more for it’s spectacle factor than actual wrestling. The young Lesnar was made to look like a destructive monster against Hogan, and pinned the six-time WWE Champion completely clean.
  • Brock Lesnar vs. Big Show (Judgment Day 2003): Leave it to someone as athletic and physically talented as Brock Lesnar to carry Big Show to one of his most entertaining matches ever. Trust me, there were no arm-drags in this match, but it is way better than what we typically get out of Big Show these days.
  • Brock Lesnar vs. Triple H (Extreme Rules 2013): Only a Steel Cage match could make a Lesnar and Triple H match interesting to me. After very sluggish encounters at SummerSlam 2012 and WrestleMania XXIX, these two beasts had a very NWA-esqe Steel Cage match that would have made Harley Race proud. It was traditional. It was a brawl. It was as good of a match you could hope for between two guys like this.


After spending over eight years away from the company that gave him his start, Brock Lesnar returned to the WWE the night after WrestleMania XXVIII.

Lesnar returned bigger and better than ever after having become a household name in the mixed martial arts most notorious promotion; Ultimate Fighting Championship.

Of course the first man he ran into was the face of WWE for the better part of the last decade, John Cena.

This was a big money feud and the match was set up to be a huge deal for the WWE, but there was one problem. Creatively speaking, both men really needed a strong victory here for different reasons.

John Cena had just suffered one of the biggest defeats in his career at the hands of The Rock, and Lesnar needed to be reestablished as the dominate monster he was being billed as. So the company had sort of painted themselves into a corner in which they were damned if they did and damned if they didn’t.

On top of this they made the match an Extreme Rules match which further cornered the company into having to have one of  the men lose despite neither man really needing to. Despite this, the match was insane.

Within moments of the opening bell Lesnar opened up Cena’s forehead after several forearm shots.

The former UFC Champion was largely the aggressor in this contest, but despite that John Cena managed to defeat the freshly returned, Lesnar. It took an Attitude Adjustment onto the steel steps to finally silence Lesnar for just him for even just three seconds.

Many argued it was the wrong call to have Lesnar lose without issue in his first big money match back in the WWE, but regardless the man looked so dominate against the WWE’s franchise player in his first match back.

Lesnar and Cena would go on to have even more high stakes matches in the WWE in 2014.


For this match, I make a few exceptions to my “rules”. It was Brock Lesnar teaming with former number one contender to the WWE Championship, Chris Benoit, taking on current WWE Champion, Kurt Angle, and his associates Team Angle, made up of fresh-faced Shelton Benjamin and Charlie Haas. How much more wrestling talent could you fit in a single ring?

Originally, Edge was supposed to be the tag team partner of both Lesnar and Benoit, but due to injury Edge had to be written out of the match. He would not return until after WrestleMania XX over a year later.

The match was a beautiful display of athleticism, but due to the chaotic nature of a Handicap Tag Team match, managed to be more erratic than polished. This made it feel more like a really entertaining Monday Night Raw main event rather than something you would typically see on a Pay-Per-View.

I’m not sure whether that is a positive or a negative, because the action in this match is just so entertaining.

This match was sandwiched between two amazing WWE Championship matches, having occurred a month after Angle and Benoit’s classic Royal Rumble match, and month before Lesnar’s career defining moment at WrestleMania.

I feel as if Benoit and Team Angle were very much the extras in this match despite doing much of the work. This was very much a match to give fans a preview of Brock Lesnar versus Kurt Angle without having the two interact too much before the main event of the biggest show of the year.

Benoit would secure the victory despite them being a man down, but it would be the young amateur wrestler from OVW who would go on to win the WWE Championship the following month


As of writing, this still remains the career defining moment in the professional wrestling career of Brock Lesnar. In all honestly, it probably always will be.

Brock Lesnar, still in his mid-20s, was being groomed to carry the WWE for the next two decades. However, not long after this it seemed as if Lesnar had grown bitter of all the time he was spending traveling and the grind got too him so much that he opted to not resign after his contract expired.

In 2003, Lesnar was still in the mindset that he was going to be the one the WWE would build around for the next decade. Brock was beginning to catch on as a babyface, and in the early months of 2003 was especially over with the crowd. While this wouldn’t last long, Lesnar was extremely well liked by fans during his pursuit of WWE Champion, Kurt Angle.

Angle walked into Safeco Field in Seattle completely beat up after spending the past four years on the road, full-time. He needed time off and surgery and, as the story goes, was advised by doctors to not wait until after WrestleMania XIX to get it.

The main event of WrestleMania XIX was made up by a talented, but severely banged up, Kurt Angle and an extremely nervous and inexperienced Brock Lesnar.

Much of this “real life” back-story was largely discussed in one of WWE’s early movie projects, The Mania of WrestleMania, which documented the days leading into the nineteenth WrestleMania event.

Famously, near the end of the encounter, the challenger ascended to the top rope. Brock attempted a Shooting Star Press, a move he did sometimes during his OVW-days, but missed the WWE Champion. The Royal Rumble winner was stunned and Angle had to almost make Lesnar kick out to cover up the faux pa.

In the end, almost as if his body turned on autopilot, Lesnar rose to his feet and hit a final F-5 and won the WWE Championship.


If you want to talk about polar opposite career paths in the wrestling business here is a prime example.

During the post Attitude Era, Edge began slowly climbing his way up the card through many injuries and setbacks. Brock Lesnar, on the other hand, went from wrestling at Ohio Valley Wrestling to dark matches to becoming the WWE  Champion within a matter of months.

Technically, this was a Handicap match which pitted the WWE Champion, Brock Lesnar, and Paul Heyman battling Edge across the pond. However, Heyman’s involvement was for storyline purposes only. It added an interesting element in that it was almost a bigger handicap for Lesnar, as he could potentially lose his title without even getting pinned.

While not as “high profile” or significantly important to Lesnar’s career as many of the other contests we are taking about today, this was a great display of athleticism by two men who went on to become hugely important to the next decade of WWE history.

Edge, a popular up-and-coming babyface at the time on WWE Smackdown!, was getting one of his first opportunities to main event a Pay-Per-View event and one of his first shots at a World Championship. This was one of those matches that made the viewer suspend disbelief every time Edge nearly pinned the champion. Going into a well executed contest that pits and obvious main event talent with a middle of the card performer makes you want to believe in the underdog.

That’s what these two men did. It was seemingly obvious Lesnar would defeat the still rising star, Edge. Yet, they made you believe that Edge could somehow overcome Heyman’s pet monster and realize his childhood dream.

He actually very nearly defeated the rookie WWE Champion, but had the match snatched from him after Lesnar utilized a steel chair to retain his title.

It would be another some four years before Edge would finally complete his journey and become the WWE Champion.


By 2004 rumors began circulating that Lesnar was over the WWE’s rigorous traveling schedule and was not looking to resign with the company. As such, the WWE needed to pass the torch to someone new who could be the babyface that fans paid to see when they came to taping of WWE Smackdown!

World traveled veteran, Eddie Guerrero, was chosen as the man who would unseat Lesnar as WWE Champion. Guerrero had wrestled in almost every major promotion in the Americas and had overcame the clutches of addiction. Charismatic, versatile in the ring, and (now) reliable, Eddie Guerrero was being set up for the biggest moment of his professional career.

Guerrero was so good because he could tell so many stories in the ring depending on who he wrestled. He was big enough that he could play the over-powering aggressor in a match with someone like Rey Mysterio, but agile an petite enough to play the evasive wily underdog in a match with someone like the WWE Champion Brock Lesnar.

Lesnar used Guerrero as a rag doll for much of the contest, but “Latino Heat” managed to ground the champion enough to keep him at bay. It would be Raw’s Goldberg that would turn the tide as the former WCW Champion stormed the ring and speared the “Next Big Thing.”

The challenger then landed a DDT onto the title and a Frog Splash to win his first and only WWE Championship.

Goldberg, who was also set to make his departure from the WWE according to the rumor mill at the time, was in attendance to start building towards their “dream match” of sorts at WrestleMania XX. It didn’t turn out that way.

However, Guerrero’s title win on this night turned out to be the greatest match Brock Lesnar never won. He’d his final WWE appearance less than two months later.


It was billed as “The Best vs. The Beast.”

This is without question the greatest match Brock Lesnar has had since returning to the WWE after an eight year absence. It was also the last time we saw CM Punk go all out on Pay-Per-View before he went AWOL in early 2014.

On paper, this looks like a total miss-match of styles and characters. However, due to both men having strong ties to the on-air character of Paul Heyman it makes perfect sense to have these two tell a story together.

The punishment that Lesnar dealt out to the much smaller CM Punk was unreal. He looked so dominate against Punk for a majority of this encounter. Only by utilizing the No Disqualification stipulation was Punk able to keep up pace with his former associate’s biggest client.

Punk turned out to be the perfect opponent to really re-establish Lesnar’s physical dominance over the WWE roster. His matches with John Cena and Triple H were a much more even playing field when it came to size and strength, but Punk had to utilize a different strategy as he knew he could not match muscle with the former UFC Champion.

His ability to outwit Lesnar was the only thing that gave him a fighting chance, but  eventually his split focus on both his opponent and Paul Heyman caught up with him.

While Punk seemingly had The Beast defeated a time or two during this contest his urge to go after Paul Heyman proved to be his downfall. The distraction of the loud mouthed manager was all the edge Lesnar needed to decimate  the more tactical “Straight Edge” superstar.

Even still, the former WWE Champion looked like a badass in defeat for hanging in the ring with a man 50+ pounds more than him. Both men came out looking better than going in. That is a pretty rare thing in all actuality.

CM Punk would later get his just revenge against Paul Heyman, but only after Lesnar struck the first blow here at SummerSlam.


This is the third match from the underrated SummerSlam 2002 card to make its way to the Pro Wrestling Countdown. That might be a record.

Speaking of records, not many men can say they won the biggest title in their company during their first year on the WWE roster. That is just another accolade we can add to Lesnar’s list of accomplishments.

At the age of only 25, Brock Lesnar unseated The Rock to become the youngest WWE Champion in history. A record that still stands to this day.

A lot of credit has to go to The Rock for  really guiding this match and helping Lesnar in his first ever Pay-Per-View main event match. You can clearly see that it was Paul Heyman and The Rock who really guided this match’s narrative.

Lesnar was still very much a freight train who was running through opponents in television matches in a matter of minutes. A main event match for the WWE Championship on a huge event like SummerSlam was a different kind of match for him at this point of time.

The WWE Champion and his challenger gave a very entertaining main event that somehow managed to not be completely overshadowed by the notorious Street Fight between Triple H and a returning Shawn Michaels that took place earlier in the night.

Despite his veteran instincts, The Rock would succumb to the F-5 and lose his record seventh WWE Championship to the newcomer from Wisconsin. This match really established Lesnar as the monster he had been booked as up to this point. It would be only the first notable victory of many to come for the NCAA Division I champion.

While Lesnar still had so much to learn in the ring and about the storytelling elements of a wrestling match, it can’t  be denied that he was a damn quick learner. Even still so new to the business Lesnar, and the people around him, knew how to acquiescent his positives and hide the negatives.

The fact of the matter was, by 2002 the company knew “Stone Cold” Steve Austin was hitting a breaking point both physically and mentally and could  see that The Rock was on his way to bigger and better things. So what do they do? Create a new star. That is all they could do.

It made all the sense in the world, whether Lesnar was ready for this huge push or not the WWE needed a new franchise player and this was their first attempt. I have to say, if put in the same position I might have banked on Lesnar as well.

Little did they know, Brock’s career path would have other things in store.


I often discuss a television match as being “forgotten, overlooked, or a hidden gem,” but this match from the tail end of Smackdown’s greatest era ever is probably the epitome of all of those.

Chris Benoit had defeated John Cena to become the number one contender at the top of this edition of WWE Smackdown!

Lesnar was doing a storyline in which he was seeking to become the “greatest” WWE Champion of all time by defending his title against many different challengers. This match was made out to be a big deal and honestly I would have shilled out money to watch a contest of this caliber on Pay-Per-View. With the brand extension in effect it meant fewer events for each brand and as such the shows had to do more to keep viewers hooked.

As Benoit was wrestling his second match of the night, Lesnar spent much of the contest in firm control of the smaller and more weary challenger. Benoit’s story of fighting from underneath and trying to outsmart and out-wrestle the WWE Champion is what built the suspense in this main event.

It was a concept that would be reused for Benoit the following year at both the 2004 Royal Rumble and WrestleMania XX.

Matches like this certainly did make for compelling reasons to actually tune in. It’s just a damn shame these two couldn’t have had more one-on-one matches together or even a longer storyline. This was one of their only notable singles matches ever televised.

These two had great chemistry. Lesnar has always gelled so well with more technically sound mat grapples, and Benoit was one of the masters of that craft.

In the early months of 2004 Smackdown’s brilliant roster took many blows. Brock Lesnar left the company. Chris Benoit and Edge were both drafted to Monday Night Raw.

Later that year Eddie Guerrero would go on to drop the WWE Championship to JBL which would eventually lead to him headlining some of the worst received WWE Pay-Per-Views of all time.


Over a decade before they stood in New Orleans’s Superdome at WrestleMania XXX, these two wagged war in a battle of “new school versus old school” inside of the dreaded Hell in a Cell.

I think this would qualify as probably the most overlooked and least talked about Hell in a Cell matches ever.

It didn’t quite make the list on Undertaker’s Pro Wrestling Countdown, but it serves as one of Lesnar’s most important victories. If you can stand toe-to-toe with Undertaker and come out the other end still intact, you have something.

The great thing about this match is that both men came out looking like cutthroat badasses. Lesnar, for overcoming a mainstay WWE performer for over a decade. Undertaker, for having a match with a dominate, young, and hungry new WWE Champion even with a broken hand.

It was the perfect story for these two to tell together.

Both men looked strong at different points in the contest, but Lesnar spent a slight majority of the time seemingly in control of the match. This was beneficial in establishing him as a strong WWE Champion and leader of WWE’s “Blue Brand” while it was still in its infancy as a individual product.

Lesnar’s rise in 2002  all the way up until he decided not to resign with the wrestling juggernaut was spent building him up as  the next face of the company. Someone who could pick up were Hulk Hogan and Steve Austin left off.

The Undertaker has rarely lost without some sort of dusty finish in which he is screwed out of the victory, but Lesnar remains the man with probably more high profile victories over The Undertaker than anyone else alive.

Lesnar has always been very much the Bane to Undertaker’s Batman.

After his strong victory over “Big Evil” Lesnar’s next  rival would be someone else’s whose athletic ability has long been the subject of praise here….


What a difference only a few months can make. This match is just about the complete inverse of their more famous main event match at WrestleMania XIX.

If you’re discussing the year 2003 in WWE history your conversation should start and end with Kurt Angle versus Brock Lesnar.

This was a marathon exhibit demonstrating just why Kurt Angle and Brock Lesnar were two of WWE’s most gifted mat wrestlers ever.

On a forgotten television match on WWE Smackdown! Angle and Lesnar managed to have a 60-Minute Iron Man Match that would surpass the quality of even Bret Hart versus Shawn Michaels at WrestleMania XII.

It was a modern take on the Iron Man match, and one that saw both Lesnar and Angle in the reverse roles that we saw at WrestleMania XIX earlier in the year.

Angle had become the fan favorite and Lesnar had become the Vince McMahon-corporate endorsed heel.

The amount of huge maneuvers used in this match to try and simply get another point on the board border ridiculous. Angle and Lesnar were aiming for the fences every moment of this match and it made for a very tense atmosphere.

Lesnar, the challenger, spent much of the match leading the WWE Champion. If Angle had 2 points, Lesnar had 3 or 4 so really the champion was the one who spent much of this match battling from underneath, which is a great spin on the normality of the challenger being the underdog and one who has to work harder to secure the victory.

In the final moments, Brock lead the match with a score of 5 to Angles 4. The champion locked in his Angle Lock on a downed Lesnar, but the clock expired with Lesnar grimacing through the pain. Despite being the chief aggressor at the end of the match, Angle lost his WWE Championship.

I thought this was a terrifically unique ending to a title match. One which still makes Lesnar look like the better man, but also makes the former champion, Angle, look damn good in the process. This is without question one of the best matches ever contested for the WWE Championship.

It also stands as Brock Lesnar’s finest performance with a man I’d consider his best opponent.

Triple H’s Top Ten Greatest WWE Matches

A hybrid performer. A man with an old school 1960s/1970s wrestling psychology, a 1980s look, and the 1990s “attitude.” Triple H really encompasses what wrestling was all about in the second half of the 20th Century.

He is the culmination of 50 years of modern professional wrestling and whether you love him or hate him the future of the industry is now, largely, in his hands.

As easy as it is to pick on “The Cerebral Assassin” over some of his life decisions and the way in which he was booked anyone who says he was handed anything obviously does not know their history.

For 25 years, Triple H has been a part of the WWE experience.  Whether he was wrestling for the WWE European Championship with Owen Hart, mocking WWE Commissioner Sgt. Slaughter with Shawn Michaels, or main eventing a WrestleMania in some of the biggest arenas across the country, Triple H has been a constant.

He is probably one of WWE’s most important talents to never effectively be the face of the company.

He has always been a rung right below the true faces of WWE. However, his talent and understanding of ring psychology have always made him one their most important commodities.

“The Game” may be one of WWE’s most unlikable personalities, but his wrestling ability and old school mentalities in the ring made him one of the 2000’s greatest and, in a way,  most under appreciated entertainers.



It’s really depressing that one of the greatest Tag Team matches in the history of WWE ended with one of the competitors suffering the worst injury of their entire career.

Miraculously, Triple H finished the match with a quad completely torn from his bone. He even was put into the Wall of Jericho on top of the announcer’s desk.

This match was wall-to-wall action and there was zero down time. Whether it was due to all four men being particularly motivated or the fact that the show was running long. It doesn’t matter. This is one of the most fast paced matches any of these four men have ever had and it was just a joy to watch.

Chris Jericho and Chris Benoit won the World Tag Team Championships from the duo and unfortunately Triple H would have to sit on the sidelines for the rest of the year.

He would not return until January of 2002 in which he would win the Royal Rumble match.

Also Considered:

  • Triple H vs. The Rock (SummerSlam 1998): This match gets a lot of attention among lists online, however compared to other encounters these two had later on this one looks a little duller in comparison. It was still a wonderful midcard match. These two helped one another get over and a year or two later later they would both be main eventing shows together.
  • Triple H vs. Chris Jericho (Fully Loaded 2000): I have a great fondness for this match and I think it’s one of the best matches of Chris Jericho’s career, but even still it doesn’t quite mean as much to the career of Triple H. This is still a great match. Triple H was one of the first guys to make “Y2J” look like a star.
  • Triple H vs. Chris Benoit (No Mercy 2000): A seriously underrated match from the string of matches that Triple H had in 2000 and 2001. He was on a roll and this was a gem among all of the other iconic matches he had at the time.


I thought these two would have a slow and clunky main event, but they really surpassed my expectations and ended WrestleMania 22 right.

I also think, historically, this was a big night for both Triple H and John Cena. Triple H had dominated the main even scene for almost four years  when he was finally sent away by his former Evolution cohort, Batista. When Triple H returned Batista had been shipped to Smackdown! and in his place was the new face of Monday Night Raw – WWE Champion John Cena.

These two had to butt heads at some point and it came to ahead in Chicago’s Allstate Arena. The man who once ruled over the World Heavyweight Championship on Raw with an iron fist challenged the young WWE Champion for the “throne.”

It was the story of the old lion battling the new lion.

It was a great story this match told, one that we could never likely see told again. John Cena was walking in as the underdog champion. He was facing the man who had largely ruled the roost of the WWE for the past three years.

Triple H was the first man to wrestle John Cena at WrestleMania and have a good match with him. Cena was still coming into his own as a “technician” in the ring and being in the main event with a guy like “The Game” was a wise move for his first headlining spot at the biggest show of the year.

The beginning of the match effectively established that John Cena could not match Triple H’s wrestling ability and when he came back to win through sheer guts and determination it sold him as a champion even more so.

At the time it felt like the company was shoving the young Cena down our throats  but looking back 2006, and this match in particular, were pivotal in establishing Cena as the main event player he is now.


The final No Mercy event was a great one in terms of main event  matches.

Honestly, I think Jeff Hardy got more out of losing this match than John Cena did winning his match with Triple H at WrestleMania 22.

Hardy returned to the WWE in the Summer of 2006 and began building momentum, moving up the card, and drawling larger and louder crowd reactions each passing month.

By early 2008 it couldn’t be ignored any longer, Jeff Hardy was main event material. After a few speed bumps, Hardy recovered and found himself headlining pay-per-view events for the first time – with Triple H.

These two had several notable television matches  in the early 2000s, but now Hardy, while still the underdog, was on a more level playing field with one of the most consistent performers of the last decade.

If “The Charasmatic Enigma’s” match with The Undertaker in 2002 was a sign that he could be somebody in the world of professional wrestling than his WWE No Mercy match was proof that he was.

Hardy was unable to “grab the brass ring” on this night as “The Game” retained the WWE Championship after rolling up Hardy after he hit the Swanton Bomb.

This loss wouldn’t kill any of Hardy’s momentum as he went on to win the title later that year. Triple H  definitely helped legitimize Hardy as he acceded into the main event scene.


This Street Fight from Survivor Series was truly the perfect playground for “The Cerebral Assassin” to exact his due revenge. Triple H beat the ever loving crap out of his idol, in Detroit.

In full disclosure, both pay-per-view matches these two had were extremely entertaining and engaging. I appreciate them both for very different reasons. Which is why I selected both of them separately, for different reasons.

Ric Flair, obviously, was far from his prime by the early 2000s. The veteran of Jim Crockett Promotions and 16 (21)-Time World Champion spent his final years in the WWE. Somehow the 50+ year old Flair managed to steal the show several times over  during his final run with the WWE.

While not nearly as spry as he was in his heyday, Flair’s knowledge of storytelling, ring psychology, and charisma allowed him to somehow thrive in the ring with men 20 or 30 years his junior. I seriously don’t think he gets enough credit for working as often  and as hard as he did at his advanced age.

Triple H was in control for much of this match and pretty much full-on assaulted the man who had been his mentor for almost four years.

They popped the crowd at all the right moments and Flair showed the right glimmers of hope that he might win only to have them shut down by the ruthless ruler of Evolution.

It was the classic “Sensei being taken down by his greatest pupil” story.


I made mention of these two’s contest for the WWE Intercontinental Championship at the 1998 SummerSlam in the Honorable Mention section. I very nearly placed that match on the Countdown, but I decided to go with one of their matches that doesn’t get mentioned as often.

In all honesty, these two worked much better matches than the 1998 Ladder match. This is definitely a more polished match with a much better story.

When you look at The Rock and Triple H, you see two men who blossomed at the same time in the WWE. They came in around the same time and they had very parallel careers during the late 1990s and early 2000s.
They worked with one another at the bottom of the card, the middle of the card, and later main evented pay-per-views together.

Really, they were both the men who battled over who should be the “second” biggest name in the WWE.

In saying that, the 1 Hour- Iron Man match might be the single most difficult match for a wrestler to pull off.

In 2000, The Rock’s popularity might have reached it’s apex, and Triple H had one of the greatest single years a wrestler has ever had. With “Stone Cold” Steve Austin gone, these two hungry men got to fight tooth and nail for who would stand above the rest in the WWE.

This position was very nearly given to the Iron Man match between Chris Benoit and Triple H from Monday Night Raw in 2004.

Although, this match serves as one of the most underrated matches in Triple H’s catalog and serves as a shining example to how good “The Game” was back then. He was the most versatile and adaptable man on the WWE roster at the turn of the century.

Triple H would win this match and regain the WWE Championship after some unintentional help from a returning Undertaker.


2007 was a wonderful year for Orton’s character, and one the best years he has ever had in his already decade long career.

Every once in awhile, usually when the WWE roster is thin, some stars have to pull double duty on a show or pay-per-view event. At No Mercy 2007, Triple H wrestled, not twice, but three times.

Orton, who was scheduled to wrestle WWE Champion John Cena in a Last Man Standing match, was awarded the title by Vince McMahon at the beginning of WWE No Mercy. Triple H took issue with Orton being handed a title and challenged him to a match. Triple H would defeat Orton for the WWE Championship and go on to defend the title against his schedules opponent, Umaga, later that night.

The newly christened “Viper” wasn’t done. He utilized his rematch clause to make the main event of WWE No Mercy a Last Man Standing match against the WWE Champion, Triple H.

Both men were still weary from their matches earlier in the night, but that desperation they displayed with their physicality was perfect for the match type they were in.

Tooth and nail. Barely able to stand. Scratching. Clawing.

This was such a unique and interesting night for both Triple H and Randy Orton. Three titles reigns in one night? Fast title changes like this should be used very sparingly, but after a year plus of John Cena as WWE Champion this one-night storyline felt very innovative and fresh.

The final match made Randy Orton look so credible and this story arc was, for me, the one that finally solidified him as the top heel in the WWE.


Few men have had more absolute classics than these two! I mean these two real-life best friends spent the better part of a decade  either teaming with one another or beating the crap out of each other.

SummerSlam 2002, Armageddon 2003, Royal Rumble 2004, and Bad Blood 2004 all featured classic contests from these two real life best friends.

When you take the emotion and grander out of that the best Triple H versus Shawn Michaels match for me took place on a forgotten edition of Monday Night Raw on one of final nights of 2003. Which just happens to be one of the worst years for the WWE’s flagship show – ever.

2003 was probably one of the most flat years WWE Monday Night Raw ever had as the premiere program for the company. Triple H and Shawn Michaels ended the year with a  bit of redemption and signaled that 2004 would be a much greener pasture for the show.

The “Heart Break Kid” and “The Game” battled in Three Stages of Hell and even a Hell in the Cell match, but for my taste their one-on-one matches were just better off without the bells-and-whistles.

This was classic Shawn Michaels battling Triple H when he was his most dastardly. He was the heel who did anything to win.

Leading into WrestleMania XX, many of the matches between “HBK” and “HHH” ended without a conclusion. That was the case here as Michaels had his former D-Generation X partner pinned, but it happened that the shoulders of Michaels were down also!

Triple H retained the World Heavyweight Champions, and the two would meet again at the 2004 Royal Rumble. Still, this gem from Raw is an absolute classic television match.


The pacing, symbolism, and brutality that was showcased inside of that cage was unlike anything you will see on WWE television today.

Neither of these two could move as quickly as they once did, but they mask that so well by building tension and selling each move like it was a knockout blow. That emphasis made every swing, kick, and hold feel so important.

That, sometimes, is the most clear difference you see with a match between two masters.

The WWE style of wrestling is much more focused on reacting to the action than it is to the action, itself.

One of the greatest philosophies in wrestling is to make all the action in the ring mean something. Doing a double moonsault or any other insane maneuver means nothing without the proper response from the other performer.

Triple H and The Undertaker understood that and lived by that in the arena.

This was as a big of a spectacle as WWE could make it. They brought out every bell and whistle they could think of. Triple H. Undertaker. Shawn Michaels. Three of the men who defined what the Hell in a Cell match was, at the biggest event of the year.

The Undertaker defeated “The Game,” again,  at WrestleMania XXVIII and marked his 20th WrestleMania victory.

This ended their trio of matches at WrestleMania that spanned a decade and truly closed  the book on and “era” gone by.


A main event contest truly worthy of being the showcase of WrestleMania’s 20th Anniversary. This is far and away one of WrestlteMania’s best wrestled main event matches ever.

Triple H had some of the best matches of his career with both Shawn Michaels and Chris Benoit. As such, it only makes perfect sense that one of the best was a match featuring both of them.

We all know the story. Chris Benoit won the 2004 Royal Rumble and instead of challenging his brand’s champion, on Smackdown!, he challenged the World Heavyweight Champion on Monday Night Raw.

Triple H and Shawn Michaels had been feuding off-and-on for almost two years and Michaels was hungry to finish the man he once called a friend. To them, Benoit was a nuisance and a thorn in their side as they tried to eliminate one another.

These ingredients produced what is quite simply one of WrestleMania’s most physical and entertaining main events ever. The story was there, the action was there, and the moment was there.

It was everything the 20th Anniversary of WrestleMania deserved.

Triple H and Shawn Michaels both helped legitimize Benoit, who had been slowly working his way up the WWE card for almost four years.

Benoit made history, and did so by making Triple H tap out to the agonizing Crippler Cross Face.

The three men would go on to have a rematch in Canada, at Backlash, a month later which we talked about in Shawn Michaels Greatest Matches.

However, this match made Triple H’s Countdown due to the enormity of him losing the title and his willingness to put over a man who had wrestled all over the world for 20 years.

Triple H, got to give Benoit his greatest moment. Even still, that’s pretty special.


Widely considered Triple H’s definitive classic, this match captures the number two position which might unsettle some readers who believe this was the best match he ever had.

This match sums up everything that made Triple H the definitive “man” during his 2000-2001 run. Sure Austin was the top guy and The Rock had better promos, but it was Triple H who was wrestling the best matches on the show.

This was Mick Foley’s definitive classic, and quite honestly the match that solidified Triple H as a top star for the next 15 years.

This was not quite as brutal as Foley’s matches with The Undertaker, The Rock, or Randy Orton, but that is in no way a critique on how wonderful this display of ruthlessness from both men.

At one point during the match, Triple H event gets his leg impaled!

Like a true professional, “The Game” sold it and worked the injury into the story of his match. Foley was always the man to put over the younger guys during the late 1990s and early 2000s.

If you notice, Triple H didn’t win his first WWE Championship from “Stone Cold” Steve Austin. He won it from Mankind. You know who else won their first WWE Championship from Mankind? The Rock.

I’m not trying to slam Austin, but more show how important Foley was to establishing two men who helped carry the roster. Foley made the future “King of Kings” look like a bonafide bad-ass in Madison Square Garden and he did it with absolute glee.

To this day, it still remains a huge turning point in the career of a man who now is instrumental in the future of WWE.


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This match very much reminds me of the match between Shawn Michaels and Mick Foley in that it is a very unappreciated classic.

The Three Stages of Hell match.

A match so difficult to pull off that over nearly 15 years there has only been four of them in total. Triple H, was in all but one of those.

I have a feeling their will be some unrest with me not placing his match with Mick Foley in the number one position, but this match with “Stone Cold” Steve Austin has gone so overlooked over the last two decades that it seems a crime to not finally give it the due it deserves.

The first fall was a normal Singles match. The second, a Street Fight. The final, was a Steel Cage match. The first man to score two victories, would be declared the winner. So, theoretically, if either Austin or Triple H won
both of the first two encounters there would be no Steel Cage match. Unfortunately for them, there was.

I think Jim Ross’s famous line, “this match is bowling shoe ugly,” is probably the most appropriate call to sum up there three falls of this match.

Austin won the first fall and, naturally, Triple H won the second. The Three Stages of Hell match concluded with both men, exhausted, inside of a Steel Cage. Triple H would win after only being lucky enough to collapse onto Austin after hitting a knockout blow.

Austin, and his Stone Cold Stunner, would get the last laugh, of course.

After this absolute war both men went on to headline one of the greatest WrestleMania events ever, WrestleMania X-Seven, with The Undertaker and The Rock in co-mainevents. Afterwards, they would form the Two-Man Power Trip and would run roughshod over the WWE until Triple H torn his quadricep in the match we talked about in the Honorable Mention section.

Thus, ended probably the most fruitful period of Triple H’s in-ring career.

Shawn Michaels Top Fifteen Greatest WWE Matches

Growing up as Michael Hickenbottom in San Antonio, Texas the future “Mr. WrestleMania” grew up idolizing wrestling greats like that of “The Nature Boy” Ric Flair. After coming through the tag team ranks of both the AWA and WWE, the newly christened “Heart Break Kid” would begin one of the highest quality singles career in professional wrestling history.

Throughout he 1990s and 2000s Shawn Michaels performed for the fans as if it would be the last time he ever stepped foot in the ring. His ability to perform was so good that it almost looked like instinct.

He might just be the most well rounded professional wrestler the WWE has ever produced. He was never the biggest draw or the greatest technical wrestler, but when it came to showmanship, match making, adaptation, and entertainment Michaels excelled on a level even other fellow greats of his time could not reach.

Shawn Michaels, more than any other performer, has appeared on multiple Countdowns, but finally we will get to look at his career exclusively and see how the matches talked about in all the previous editions stack up against one another.

This was difficult, as some of  the matches and performances talked about here are some of my favorites of all time.

Lets look back at a career filled to the absolute brim with some of the greatest professional matches ever contested in a four-sided ring.


An opening match in the 2005 Gold Rush Tournament. This was a tournament created by Eric Bischoff to crown a number one contender for the new World Heavyweight Champion, Batista.

Sometimes, when I hear praise for this match I often feel it is simply for the amazing finish in which Michaels hit Sweet Chin Music on a mid-air Shelton Benjamin who had just spring boarded off the top rope. However, I feel like, the other 15 minutes of the match were just absolute – well -gold.

The match very much falls into the same category as a Bret Hart/1-2-3 Kid or Undertaker/Jeff Hardy match that took place on WWE Raw.

A big name main event star having a match with a talented mid-card performer in which the latter loses but comes out of the match looking much more valuable to the product than before.

Shelton Benjamin spent much of the match one upping the “Heart Break Kid” by beating him to the punch as Jim Ross said. Shelton Benjamin gave Shawn Michaels everything he had. The Dragon Whip and all of his other crisp offense could not keep Michaels down for a three count.

Finally, Benjamin popped off the top rope from the outside to try and catch the veteran off guard, but the instinct of Michaels kicked in, and Sweet Chin Music finally found it’s mark.

After the match, the Texan patted the downed WWE Intercontinental Champion on the chest in a sign of respect.


More than any other match on this list, the main event of WrestleMania XIV is probably most famous for all the things going on behind the scenes with Shawn Michael’s injury and his miserable backstage attitude.

For that reason, and the fact that you can see Michaels in pure agony all throughout this match, I nearly left it off completely. Then I remembered how important this match really was.

This was one of only two or three times that these two ever wrestled one-on-one. It was also the visible transition from the Michaels/Hart era to the Austin era.

Sometimes I wonder what this match would have been like had Michaels not been on his way out. Still, broken back, or not, these two gave WrestleMania a great main event. This was probably the first truly successful WrestleMania main event since the end of the Hulkamania Era.

After finally winning the WWE Championship Austin took his rightful place as “the man” in the company.

“Mr. WrestleMania” may not have wanted to do the j.o.b. but he did so. He may not have been gracious about it, but in the end he put Steve over and he did it beautifully.

The crowd was into the story these two told and Austin finally got the accolades he had worked so hard for. This would be the last time Michaels performed at a WrestleMania for five years and we wouldn’t see him compete in a WWE ring at all for over four years.

He would come back to the ring in 2002, better than ever. Unfortunately, for Austin, by 2002 he had only a handful of matches left in his tank.


This match got huge points from me for being so unique.

The gimmick for this match was so subtle, but did so much to make their encounter stand out.

Shawn Michael’s Sweet Chin Music was banned, and if he used it to try and win the WWE Championship from Randy Orton he would forfeit the match. Conversely, if Randy Orton was disqualified in any way, then Shawn Michaels would be awarded the WWE Championship. I have never been a huge fan of Randy Orton’s wrestling ability, but this has to be one of the most underrated matches in the “Heart Break Kid’s” monumental catalog of matches.

The result was Michaels breaking from his traditional formula and giving his fans a very different experience. 2007, Randy Orton was at his very best. From both an in-ring and character perspective he has never been better – before or since.

The stipulations added a great dynamic in which Orton would taunt the “Heart Break Kid” to use his superkick and Michaels even teased it several times to the shock of Orton.

Because his finishing maneuver was banded the Texas native broke out many maneuvers he did not use often and wrestled a match that would certainly look like a black sheep compared to his other lofty performances.

That is not a critique, it’s a compliment.

Despite breaking out the Crossface, the Sharpshooter, and even an Ankle Lock, Shawn Michaels could not defeat Randy Orton in Miami.

But after his defeat, Michaels got his revenge in the form of the Sweet Chin Music he had so desperately wanted t0 use the entire match.


I think Jannetty and Michaels just worked so good in the ring that they were better opponents than team partners. They were pretty good tag team partners too, so that sound come across as praise already.

A match so good, it won Pro Wrestling Illistrated’s Match of the Year award. An award Shawn Michaels would go on to win 11 times after winning it for the first time, here.

This will definitely be the most obscure match we will talk about today, but it still deserves to be recognized as one of Shawn Michaels earliest “great” one-on-one matches.

I have a strange love for several matches from the stretch of 1993 to 1994; the early days of Monday Night Raw.

Matches involving Razor Ramon, The Undertaker, 1-2-3 Kid (who made his debut on this very edition of Raw), Mr. Perfect, Ric Flair, Doink the Clown, Bret Hart, and many others. Watching these matches is like looking into an old toy box that was forgotten in the attic.

Shawn Michaels versus Marty Jannetty is another one of those early Raw matches that I have a tenderness for.

Marty Jannetty now joins Sabu on the list of “guys I never thought would be featured on the Countdown.” Really though, his matches in the early 1990s with Shawn Michaels were absolutely wonderful. It showed they had not only chemistry as a tag team, but as opponents as well.

This particular match was for the WWE Intercontinental Championship after Michaels had challenge a anyone to try and take his title from him and out came his former tag team partner in disguise. To the shock and chagrin of a heel “Heart Beak Kid,” Jannetty would prove to be just as formidable as an opponent.

With the help from a distraction from Mr. Perfect, the former Rocker pinned the newly christened “Heart Break Kid” and become the first man to win a championship on WWE Monday Night Raw.

These two had a ton of great television matches, but the crowd was never hotter than during this one.


After five long years of being away from the WWE ring, “Mr. WrestleMania” came home. And he didn’t disappoint.

Inside the enormous Safeco Field, Shawn Michaels battled Chris Jericho for the first time; one-on-one. It would be far from their last.

On a card stacked with main event caliber matches, like Mr. McMahon versus Hulk Hogan, The Rock versus “Stone Cold” Steve Austin, and Kurt Angle versus Brock Lesnar, Shawn Michaels and Chris Jericho reminded us all that you didn’t have to be top billing to put on the match that people would be talking about for the next decade.

As I’ve talked about in the past, the brilliance of this match was that these two managed to stand out on a card dominated by stars far bigger than them.

Their chemistry was apparent and the story going into the match made it all the better. Anytime a character can come across through their actions inside the ring you know a talent is into what they are doing. Jericho played the jaded jealous former-HBK fan to a tee.

Shawn Michaels would win a very competitive and entertaining match, and got a kick to the groin from a frustrated “Y2J” for his trouble. Jericho, who wanted to step out of his shadow, failed to live up to his own expectations.

This would be far from the last time we got to enjoy these two’s ability to tell a story.


I would venture to say that no match in WWE history brings about more division among fans than this one. Is it as good as everyone says? How important was it really? Did Michaels and Hart really have one of the best WWE Championship matches or did they just manage to wrestle a 60-minute match?

My opinion of this match is that every professional wrestling fan should watch this – ONCE.

However, this has to be one of the most difficult matches to re-watch for writing purposes. What this match does do is put over the WWE Championship as the absolute biggest prize in all of professional wrestling. Few other big banner matches have put over that title’s importance like this one.

That might be why it is often in the discussion as one of the greatest WWE Championship matches ever.

The inherent problem is that a great ending to a wrestling match is one that usually comes, as WWE Hall of Famer Jim Ross would say, “out of nowhere.” However, in the Iron Man match you have to find a new way to create that spontaneity so the crowd will still pop.

Michaels and Hart wrestled a beautiful match and showed that they were the most talented men on that particular WWE roster.

That was not big challenge for them, but what they could not do was give the fans a typical five star masterpiece filled with re-watchable sequences that we all love from so many of the other classic WWE matches.

This match is a very unique animal all the same.


This might be one of the most unappreciated classics that WWE currently has in it’s deep vaults of footage. I got to gush about this match a ton last season, but this match means very different things to the career of Shawn Michaels than it does to the career of Mick Foley

The “Heart Break Kid” might be one of the best professional wrestlers to ever live and he has given many men some of their greatest matches. In turn, those matches might not necessarily be good enough to be featured among Shawn Michaels’s greatest.

I think it should be a huge feather in the cap for Mick Foley to know that he had a match with Shawn Michaels that fans consider to be one of the Michaels’s greatest performances and not just one of his own.

This, however, is definitely a black sheep when you set it among all the other great silky smooth performances of “The Showstopper’s” career.

It is almost grungy and brutal in it’s execution, but then again this match was held in Philadelphia and Michaels was performing against possibly the most successful “hardcore” wrestler to ever live.

Michaels did not have to carry Foley to have a great match, but the two threw their wrestling styles at one another and what we got was a painting with beautiful contrast.

I absolutely adore this match and anyone who has never seen it needs to seek it out.


If this Countdown had been over Chris Benoit it would have certainly been a lot harder to not opt for the amazing Triple Threat match at WrestleMania XX.

Today we are looking at the career of Shawn Michaels and when you take the emotion out of the WrestleMania match it’s story is just not as interesting as the one that took place during the Backlash 2004 rematch.

Truth be told, they are both amazing matches without a doubt, but the role Shawn Michaels played in this one was so much more prominent. He almost felt like a third-wheel at WrestleMania, but at Backlash the fans could certainly notice him.

This match took place, not in New York City, but in Chris Benoit’s hometown of Edmonton, Alberta, Canada. At this time, the WWE’s Canadian fans were still pretty sore at Shawn Michaels for a certain event that occurred in Montreal a few years prior.

Obviously Michaels played up his heel antics and as such and it made his role in the match, and the match in general, much more interesting.

There was one point in which Michaels, accidentally, knocked out the referee and then locked in a Bret hart-like Sharpshooter on Benoit. As he has the move locked in out comes, who else, WWE Senior Official; Earl Hebner. The fans drowned the arena with “boos” of “You screwed Bret.” It was wonderful.

In a beautiful tribute to the 1997 Survivor Series, Chris Benoit retained the World Heavyweight Championship using the Sharpshooter on Shawn Michaels.

Seeing these three men wrestle together really sent your emotions for a roller coaster ride. It’s a damn shame we only got to ride it twice.


For some reason, this match elicits a lot of mixed feelings from fans of the WWE, especially online. Part of me thinks it has to do with John Cena.

Regardless, I think this is the single greatest television match HBK has ever participated in.

He had so many wonderful matches on WWE Monday Night Raw after he came back from his near career-ending back injury with the likes of Triple H, Chris Benoit, Shelton Benjamin, Jeff Hardy, Mr. Kennedy, and numerous others.

I do feel, though, that his match in London, England with the WWE Champion, John Cena, is far and away his best free television match ever.

It’s so rare that a TV match between two competitors is better than one of their pay-per-view matches, especially one that takes place at WrestleMania. This was one of those cases.

They wrestled an hour long Broadway before, finally, Michaels found a brief opening.

In the end Shawn Michaels somersaulted out of Cena’s final F-U and hit Sweet Chin Music, as Jim Ross would say, “out of nowhere.” Michaels was only so lucky that when he fell it was on top of the dazed WWE Champion.

This match was not even for the WWE Championship. It was all bragging rights.

It was all based around pride and ego. WWE always puts there best foot forward when it comes to giving the overseas fans some of the best television matches of the year, and this is the chief example of that.


To me this match is like a bad ex-girlfriend that I can’t decide if I still want or not.

Sometimes I love it and want to watch it over-and-over again and other times I find it to be the most overrated piece of garbage I’ve ever watched.

“I used Shawn Michaels to get to the top, just like Shawn Michaels used me to stay at the top.” – Triple H

If a tag team or stable is successful in the wrestling business you can bet at some point it will break apart and it’s members will feud against one another.

Shawn Michaels and Triple H took that to a whole new level in 2002 . They met for the first time at SummerSlam and their war ragged on-and-off for the next two years.

I feel like I’m including this match here for largely sentimental reasons which I usually go against. Truth be told, it is an excellent brawl on it’s own merits, but the goosebumps I got seeing Shawn Michaels wrestle for the first time in over four years eclipsed everything else going on here.

It was simply the most unbelievable WWE comeback ever. Only a return of “Stone Cold” Steve Austin would surprise me more than this did.

Shawn got the victory and came back and had a banner eight year run with WWE. Not bad for a man who had broke his back less than five years earlier.


The story Shawn Michaels and Chris Jericho told in 2008 was almost like a spiritual sequel to their 2003 story.

In 2003 Jericho wanted to step out of the shadow of his former idol, and in 2008 he come back seeking to destroy him.

This was the most carefully told and brilliantly executed story the WWE has constructed since the end of the 20th century. Nothing else in the summer of 2008 mattered to me expect what these two were doing.

I would venture to even say the brilliance of their rivalry was even what motivated me to start writing online about professional wrestling on a regular basis.

At this point, Shawn Michaels and Chris Jericho knew each other well. They had wagged war many times in the past, and really, this was their final major one-on-one match together, and how apropo it was that it was in a Ladder match.

The two men, I believe, had the smartest Ladder match ever. There has definitively been Ladder matches with better spots and more sleek sequences, but no Ladder match had more logic or interesting storytelling as this one.

Chris Jericho would get the last laugh defeating Shawn Michaels in the match that he used to make himself famous.

The two would have one final match on Raw the next year, but as far as anyone, with any taste is concerned, this was the end to over five years of history.


Both are so good, and similar enough, that I decided to cheat and give the number four position to both. I did this instead of taking up two positions with their matches because of how alike they are. So, yes, this is a cop-out.

Let me explain more why I crammed both together and didn’t leave either off.

The match from WrestleMania X is both innovative and iconic. There match at WrestleMania is clearly the more historically important match, but I still feel the SummerSlam match was worked much better. Leaving either match off would be a glaring omission for me.

They are also too similar to be given two separate individual positions like some opponents are given.

To me, Shawn Michaels established Scott Hall as an icon of the New Generation Era. I’m only sad that we never got to see “The Bad Guy” achieve more in the company that he made his name in.

Razor Ramon and Shawn Michaels worked so well together, and many accuse Hall of just being so lucky to be in the ring while Michaels “wrestled a ladder.”

Scott Hall, however, was trained by Dusty Rhodes, Barry Windham, and was broken in under the watchful eye of Curt Hennig in the AWA when the two men tag teamed together.

By the time “The Bad Guy” had reached the WWE he was more than capable of keeping up with a young Shawn Michaels.


Placing this match anywhere but number one feels so cumbersome to me.

I feel as if I could very easily give this the number one position and sleep with no problem, but I still think this is the fairest position I can give it.

This was high drama at it’s finest and a shining example of how less can be more. There is “laying around” in a match and then there is selling the emphasis of your opponents blows while building the crowds anticipation. This match featured no “laying around” as far as I’m concerned. Every second meant something and contributed to the larger story the two men were telling.

To be honest there was not much story to go on as the match was hyped up. Did we really need any reason to want to see the two longest tenured WWE performers of all time duke it out in their home state of Texas at the 25th Anniversary of the biggest wrestling show of all time, WrestleMania?

No. We didn’t.

We all knew Michaels and Undertaker would give us the most well crafted piece of performance art of the evening and they still surpassed our already high expectations.

Seriously, what more can be said about this match? It has become the new age Steamboat/Savage of the modern era of WrestleMania. And yes, it gets way more credit than it probably deserves just like Steamboat/Savage did.

Fact remains, it is one of the easiest to watch matches ever and it gets huge points for being between two of my favorite professional wrestlers.

It also took place in Texas, between two Texans, at the 25th Anniversary of WrestleMania. How much more perfect can that get for a wrestling fan from Texas? This match was tailor made to please me.


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I’m not sure if it is possible to wrestle a “perfect match,” but it is damn hard to think of anything that Kurt Angle and Shawn Michaels missed here.

After his two year odyssey with Triple H finally came to an end, Shawn Michaels was sort of left in limbo. Enter Kurt Angle.

The WWE Raw superstar and the WWE Smackdown! superstar met by chance in the Royal Rumble match where Angle was quickly greeted by the cold mistress that is, Sweet Chin Music.

That is all the reason the furious Olympic Gold Medal winner needed to challenge every accolade “The Showstopper” had ever collected while spending the weeks proceeding their first encounter mocking Michaels by defeating his former tag team partners and signing his entrance song with his former manager before putting her in an Angle Lock.

The two men would systematically steal every show they performed together on.

Whether it was underneath the HOLLYWOOD sign at WrestleMania 21, among the bright lights of Las Vegas at Vengeance 2005, or back “home” on the USA Network during Raw’s “Homecoming.”

They outperformed everyone. Every time. And they made it look easy.

It was on the grand stage of WrestleMania, of course, that “Mr. WrestleMania” once again showed everyone why he was the single greatest performer in WWE history. It was their first meeting, and their most entertaining meeting.

Kurt Angle would force Shawn Michaels to tap out while “the lights were on bright”, but that would be far from the end of it.

What has really always made me love this match is how Michaels adapted his style and kept up with, and even excelled in the ring with, one of the most talented ring workers in the company at that time.


You have two of the most important WWE superstars of all time in their prime. A brand new innovative Hell in a Cell match. Wall-to-wall action. An engaging storyline based around The Undertaker getting revenge against Michaels.

On top of all of that quality, we see one of the greatest debuts in WWE history with the introduction of Kane thanks to Paul Bearer.

Everything was executed to perfection in this match.

For my money, this is the benchmark that all other WWE matches should be judged against. Booking, storyline, in-ring dynamic, action, reaction, and wrestling are what make a match what it is. Even the swerve at the end with Kane was just fantastically over the top. This match hits, nay surpasses, all expectations when judging it on that criteria.

D-Generation X was just beginning to blossom and Shawn Michaels was embracing a new attitude that stood in stark contrast to the beloved “Heart Break Kid” of old.

The characters. The athletes. The wrestlers. Whatever, Shawn Michaels or Undertaker you are referring to, they gave just about as close to perfect as any WWE match has ever been.

It was a classic despite the fact that it was inside of a gimmick cage. That was just the cherry on top.

It was the “WWE Style” personified.

Undertaker went to finish off Michaels, and exact his righteous revenge, but the lights dimmed and the music of Kane sounded for the first time.

“That’s got to be Kane!” -Vince McMahon

Kane made his way to the Cell, and, to the shock of Undertaker, delivered a Tombstone Piledriver to allow the bloody WWE European Champion the victory and a chance to face Bret Hart…at Survivor Series.

Even narrowing Shawn Michael’s greatest matches down to 15 instead of ten, was extremely challenging when you consider the fact that he is second to no one when it comes to combining all the elements of sports entertainment.

Storytelling, in ring prowess, charisma, and character building are all elements of sports entertainment that Shawn mastered and combined flawlessly to become the greatest of all time.

The Undertaker’s Top Ten Greatest WWE Matches

Over the past three decades there has never been a professional wrestler that has stood the test of time better than The Undertaker has. He truly is the bridge that gaps generations in the WWE. Undertaker’s gimmick was supposed to be just another goof ball, out of this world, gimmick that the WWE was making a lot of their performs use at the time. However, the man under the black hat has turned into one of the most legendary characters to ever be seen in the company.

Undertaker has endured through the years because of his ability to move around the ring like someone half his size usually would and his ability to adapt with the times. He is a cornerstone of the WWE and someone the fans truly respect. He will go down as one of the most iconic and important figures in WWE forever.

The day that Undertaker finally decides to walk away forever will truly be a turning point in the history of professional wrestling. I fear that day draws closer and closer, but I take great care to enjoy every moment we get to see “The Deadman” perform.

While most professional wrestlers tend to stick around long after their prime Undertaker has managed to keep himself around this long by working a limited schedule in recent years (and now usually only once a year) and refusing to give the fans no less than his very best every time he walks in the ring. Even if it damn near kills him. He has wrestled some of the greatest names of all time in the business and no matter what was going on in the WWE, Undertaker was always there.

He has aged like, in the words of Jim Ross, a fine wine as his ability to have terrific matches has only increased as time has worn on. So today, I will look at ten of the best matches of a career filled with legendary bouts by one of my all time favorite professional wrestlers.

Let us look at only a small portion of the legendary career of The Undertaker…


The first WrestleMania match that would lead into a resurgence in The Undertaker’s wrestling ability.

Randy Orton, at the time going under the nickname “The Legend Killer,” had lain waste and spit in the face of some of wrestling’s biggest legends. From Harley Race to Mick Foley, Jake Roberts, and Shawn Michaels. The third generation WWE superstar showed he had no care for the forerunners of the professional wrestling business.

So, naturally, taking on Undertaker and his undefeated WrestleMania streak was a natural step in the evolution of Orton’s character. The match was built up very well with Orton’s father and former WWE superstar Jake Roberts pleading with him to rethink the match with the dangerous veteran.

The match was the first of many WrestleMania matches which would be centered around Undertaker’s loss-less WrestleMania record, and the feeling was at the time that Orton would end it in Los Angeles.

Even with his best efforts and fantastic match, Orton fell to The Undertaker after trying to use his signature Tombstone Piledriver. The crafty veteran reversed the maneuver into a Piledriver of his own and secured his 13th victory.

Also Considered:

  • The Undertaker vs. Ric Flair (WrestleMania X-8): This match was better than it ever had any right to be on paper. Ric Flair was over the hill  and The Undertaker had grown a reputation as being very stale in the ring, but both men came to Toronto and put on a vastly underrated brawl that to this day remains a gem among The Undertaker’s WrestleMania matches.
  • The Undertaker vs. Brock Lesnar (No Mercy 2002): I always say that this is probably the most  overlooked  Hell in a Cell match in WWE history. Lesnar  and Undertaker had a blood bath, and “Big Evil” really helped legitimize the young WWE Champion as he was preparing to be the top dog on the newly established second brand of WWE; Smackdown!
  • The Undertaker vs. CM Punk (WrestleMania XXIX): After spending  almost half a decade wrestling real life best-friends, Shawn Michaels and Triple H, The Undertaker finally got a chance to wrestle someone new, a more modern WWE Superstar. That man turned out to be CM Punk, who was fresh off a groundbreaking 400+ day reign as WWE Champion. The match was incredible and stole the show, as expected.


10. Undertaker & Batista.jpg

While I mentioned Undertaker’s WrestleMania match with Batista would not be featured in this Countdown, I did however want to recognized their rematch a month later at Backlash. To me, this is the best match these two ever had.

Even their wonderful match at Cyber Sunday was unable to eclipse this one in my mind. I always thought that Batista could only have good matches when he worked with the right guy, and Undertaker really knew how to pull a stellar performance out of “The Animal.”

This was a Last Man Standing match, and I thought this was a perfect stipulation for these two to work within. Batista was selling a leg injury at this time, but I really felt like this added a great dynamic too the match and made Batista look strong as he kept getting back up before the then-count despite his injuries.

This match was all about high impact moves and using the environment to put the other man away. Announces tables, steel steps, folding chairs, and alike were used by both men to try and keep the other down for a ten count. Time after time in this match either Batista or Undertaker crawled up just a second shy of the 10 count. This, while hurting the pacing of the match, really built of the suspense and drama.

The match ended in a double count out, with a huge set piece that Batista speared Undertaker into. I felt the ending was very corny and this match might have ranked higher if it had not been plagued by these issues. However, the action that took place in this match and the emphatic scaled pacing more than makes up for its shortcoming.

Batista would finally defeat Undertaker, beyond a shadow of a doubt, later that year at Cyber Sunday.


10. Undertaker & Hardy.jpg

This is without a doubt Undertaker’s best Monday Night Raw match in his storied career. It may be one of his most beloved matches as well. This match is also notable for being Undertaker first ever ladder match and I could think of few men better to bring “The Deadman” into the match than the charismatic daredevil, Jeff Hardy.

It is always a joy to see a familiar WWE superstar in a new element like this, and this is a perfect example of that. Undertaker was known for being a brawler and this I believe was a great move for him that really showcased his versatility and willingness to adapt in the ring.

This match did a ton for both performers. It put over Undertaker as a ruthless and dominate champion while also showcasing the guts, determination, and passion of Jeff Hardy. The contest was full of a lot of unique ladder spots, but aside from that the contest had a really big fight feel to it. The fans lost it when Jeff nearly succeed in garbing Undertaker’s WWE Undisputed Championship.

The match came to it’s conclusion when Undertaker finally put Hardy away with a chock-slam off to top of the ladder.

Undertaker was not done, however, as he reentered the ring and delivered a Last Ride to the high flyer.

As “Big Evil” rode his motorcycle to the back a injured Jeff Hardy proclaimed that “You haven’t broken me yet. I’m still standing” Undertaker returned to the ring once again and instead of attacking the young up-and-comer raised his hand as a sign of respect.

Jeff Hardy has gone on record saying that this was the match that truly launched his singles career, but Hardy deserves credit as well for giving Undertaker one of his best matches of all time.


This match is something the WWE rarely has the patience for these day. A feud with a long build-up to the first match. The Undertakers brother, Kane, made his WWE debut in October of 1997, but The Undertaker and Kane never had a single match until March of 1998 at WrestleMania XIV.

The WWE spent fives months building the suspense of the fans and constructing a story that would keep the fans interested for not just mere weeks. They put time into making the first match The Undertaker had with his brother a big deal. They waited to have the match at WrestleMania.

The art of constructing a long and interesting storyline that builds suspense and anticipation in the fans is dying. We saw a resurgence in this style with The Rock’s match with John Cena being announced a year in advance, however the story was on the back burner for a large portion of that year.

This match was built around a great, surreal, if not corny, story that boiled for months and months and the pay off, the match, made all that waiting worth it. There is so much intensity in this match. You feel every punch and it feels as if every move could shake the entire arena.

This, to me, is the greatest big man vs. big man match of all time. It is so easy for two big guys to have slow paced boring match. Several of The Undertaker’s previous Wrestlemania matches are bad good example of this.

His matches with Giant Gonzalez, King Kong Bundy, and even Sid Vicious were all pretty terrible. However, Kane and The Undertaker had a fantastic match full of high impact moves and brutal brawling action.

They also owe a lot of credit to the fantastic build up this match got and the time they had to develop the feud. Kane was viewed at the time as Undertaker’s biggest threat to date and the fact that he dominated “The Deadman” during a majority of this match really convinced me that he could be the more dominate monster.

The two did things in this match that most 7 feet tall men couldn’t dream of doing in the ring. At one point The Undertaker ran towards Kane and he caught his older brother and put him on top of his shoulders before slamming him down onto the mat.

Near the end of match Undertaker had still not been able to knock down his brother and attempted a suicide dive onto Kane who was on the outside. However, Undertaker missed and went crashing through and announce table.

The match finally ended after Undertaker preforms a Tombstone Piledriver  on  Kane for the third time. Out of all of  his Wrestlemania matches he has never taken more punishment than in this match. This is how all seven-foot giants should wrestle.


This match occurred ten years after Undertaker’s epic clash with his tormented brother, Kane. This time the cagey veteran walked into WrestleMania as the main event of the stacked card for the first time in over ten years.

I really feel like this match is forced to fly under the radar of Undertaker’s other iconic WrestleMania matches with Triple H and Shawn Michaels, but this was one of the most well done main events in the past ten years of WrestleMania.

I remember being taken aback by how much offense Edge got in with little in return from Undertaker during the beginning of the contest. However, to me it really helped build up the match and aided in establishing Edge as a menacing threat to “The Deadman’s” Wrestlemania record. This really worked well.

“The Ultimate Opportunist”  had screwed Undertaker out of the World Heavyweight Championship and managed to dodge him at every turn over late 2007 and early 2008, but Edge couldn’t hide forever. Walking into WrestleMania XXIV Edge was even able to drag that Undertaker had never defeated him.

Edge threw everything but the kitchen sink at the legendary performer, but Undertaker came back at the end and locked in the Hell’s Gate after no selling Edge’s spear. This back-and-forth contest really showed off the fact that Undertaker doesn’t need a gimmick to have an engaging match.

In the end Undertaker became 16-0 and regained the World Heavyweight Championship. The two would go on to feud for a majority of the summer.


Like several matches on this Countdown this match has some historical importance.

While this event is mostly remembered for the match were Steve Austin broke his neck after Owen Hart botched a piledriver the main event between Hart and The Undertaker is one of Taker’s most underrated matches I’ve ever seen as I really enjoy the way the two of them work together.

I loved Bret as a heel. It also made Undertaker that much better of a babyface. Also the spot where the Hart Foundation comes out really helps sell the fact that The Undertaker is fighting an uphill battle.

While I don’t enjoy run-ins typically it worked well to highlight this match. Hart, being the revered mat technician he is, spent a majority of the match working on the WWE Champion’s legs. This slowed Undertaker down making it more difficult for “The Phenom” to hit a majority of his finishing maneuvers.

I felt the addition of Michaels as referee was a bit unneeded and an obvious plot device, but it didn’t distract too much attention from the in-ring action until the conclusion.

The end comes when Bret spat in Michaels face leading to “The Heart Break Kid” trying to hit Hart with a steel chair and missing and hitting the champion. This of course gave Hart the opportunity to pin Undertaker and win the WWE Championship.

On this night Bret “Hitman” Hart would win the WWE Championship for the very last time and how ironic the man who helped him win it would be the same man who would take it from him. Shawn Michaels. The ending to this match lead to a number one contender ship match at Bad Blood between The Undertaker and Shawn Michaels in the very first ever Hell in a Cell match which Michaels would win after the debuting Kane took out The Undertaker.

After that Shawn Michaels challenged the WWE Champion, Bret Hart, at Survivor Series and the rest, as they say, is history…


Is it overrated? Yes, but so are many of WrestleMania’s best contests.

The Undertaker walked into WrestleMania XXVIII for the 20th time against Triple H, in their third ever Wrestlemania encounter. This match was made even more special with the addition of Shawn Michaels as the special guest referee and the stipulation of Hell in a Cell.

The Undertaker and Triple H are almost unarguably the most experienced WWE preforms inside the cell so I knew this mach was going to be extremely spot on.

I considered all three of their WrestleMania matches when putting together this list, and I had a very difficult time deciding on which one I wanted to showcase at the number six position. I really enjoyed their dramatic showcase at WrestleMania 27, but I felt that match was overly-long so I eliminated it first. That left me with their Hell in a Cell match at WrestleMania XXVIII and their first ever one on one match at WrestleMania X-Seven.

Previously, I considered their WrestleMania X-Seven match one of Undertaker’s absolute best, but I feel after a decade the match has not aged as well as some other matches of that time. While still a wonderful match I feel like Undertaker and Triple H truly reached the pinnacle of what they could do in a ring together at WrestleMania XXVIII.

Brilliantly paced, very brutal considering the toned down era we are currently in, and a perfect conclusion to the story of Triple H and Undertaker. This match really worked perfectly for WrestleMania XXVIII and the two veterans really maximized their strengths and minimized their weaknesses in this showcase.

I will admit that this match took some time to grow on me, but after repeated viewing I see why everyone loves it so much. The “End of the Era” match was a celebration of what made the last 15 years of the WWE so special.

I honestly thought this could have been The Undertaker’s final  match and if it had been I think this would have been a fantastic way to go out.


This match has really gone under the radar in recent years, but truth be told it is one of my favorite three way dances of all time.  In fact the only triple threat matches I like better are the Unbreakable and WrestleMania XX  triple threat matches. This match was for The Undertaker’s Undisputed WWE Championship and to be bluntly honest there is not too much of a memorable story to go along with this match. I think it is just as well as it allows you to focus on the very interesting dynamic the three employ together.

At the time The Rock had just begun his film career and was at the peak of his popularity. Kurt Angle was having some of the greatest matches with WWE’s most talented wrestlers and accomplishing more in 2 years than most WWE stars accomplish in a lifetime.   Finally,  Undertaker was the Undisputed Champion and the most physically dominate and intimidating guy in McMahon’s company.

So we have three of the greatest performers in the WWE , at the same time in the main event for the Undisputed Championship, and they bring it to say the least. near the end of the contest all three men used each other’s own finishing maneuvers after their own were not enough to win the title.

Watching the three guys go at it is very interesting as the all have very different ways of pacing a match, but somehow they all manage to stay on the same page and wrestle at the same pace. It follows the tried and true formula that most three way dances employ, but unlike others this match does not abuse that redundant concept.

I’m referring to the formula in which one competitor will get knocked out of the ring while the two other wrestlers carry on until the third rejoins the fray and knocks another man out. Rinse, and repeat, until someone wins.

That  formulaic pattern sometimes becomes distracting, but it really is not that noticeable here, and I have few problems with this match at all. It is a joy to watch, and while it has no heavy iconic story to go along with it the match is simply and entertaining back-and-forth wrestling match.

The match ended with The Rock pinning Kurt Angle after the Rock Bottom. Undertaker tried to break up the count but he was just a moment too late. The Undertaker would not hold another world championship for almost five years when he defeated Batista at WrestleMania 23.


Is this match overrated? Of course it is. Is it a masterpiece of performance art and one of the best WrestleMania matches of all time? The answer to that, is the same as the answer to the first question. So yes, this match is wonderful, but I think far too many wrestling fans fawn over it for the wrong reasons. To be honest I had a little trouble deciding which WrestleMania match I wanted to pick for the number three position in this Countdown.

Both of  Undertaker’s matches with Shawn Michaels at WrestleMania are fantastic, but I only wanted to have one on this list.

The reason I went with the first match was because I genuinely thought this match had the better in-ring action, even if it did feature a few awkward botches. Yes, I know I just critiqued Shawn Michaels vs. Undertaker. Don’t point that gun at me. I understand this match is special  to many people, but it is not flawless. Still, even if their rematch was a little more crisp, I thought this match was paced miles better and the Houston crowd sold this performance beautifully.

I will admit that the story and build up to the match at WrestleMania XXVI was much better and there was more emotion attached to it and I think more people cared because it was almost a sure thing that it would be Shawn’s last match. Still I stand by my decision. This match deserves to be here.

There was magic made on this night in Houston, Texas.

I’m sure there will be plenty of people who prefer their WrestleMania XXVI match due to all the emotion and hype around it because it was Shawn’s final match. However, I rarely find myself siding with the majority.

The Undertaker and Shawn Michaels not only met people’s expectations, but they blew them out of the water. On this night they stole the show and no one will be able to have a conversation about WrestleMania 25 without discussing this now iconic match.

To me this is the defining match of this era. The same way that Hogan’s match with Andre defined the “Golden Era”. Regardless of which WrestleMania match I decided on no one can argue against the fact that Undertaker’s WrestleMania matches with Shawn Michaels will go down as some the greatest matches of this decade and maybe even all time.


In my opinion this was Kurt Angle’s last “great” match during his seven years with the WWE, and while Angle had several memorable contests with Undertaker I felt none of them could  eclipse this one.

For my money this is one of Undertaker’s greatest one on one matches ever. I think it gets some hate because it moves a little slow in the opening minutes of the match before Angle and Undertaker begin to really bring some intensity to the contest.

Both men pick a part of the body and spent the rest of the match focusing on wearing down that part of the body.

The Undertaker started working on the shoulders of Angle, but he wasn’t able to maintain control because Angle began to work on the knees on Taker. Our “Last Outlaw” would spend a majority of the rest of the match trying to keep up with the World Heavyweight Champion.

After being slowed down by Angle’s constant assault on his knees,  Undertaker spent much of his energy try to land high impact moves to put Angle away. This tactic holds Angle off, but not for long.

Every time”The Deadman” tried to hit a big move Kurt Angle would counter out of it and bring him to his knees. This is an interesting match because in most of his matches Taker is usually the chief aggressor. So seeing him play defense in this match was a welcome dynamic.

I think this was WWE’s way of building up Kurt Angle as World Heavyweight Champion going into WrestleMania 22. Which is why we saw Angle in control for so much of the match. It worked really well in putting over Angle as a dominate champion while not ruining any creditably of Undertaker.

Angle seemed to have a huge sense of pride as he had a chance to win via count out, but he made the referee stop counting and allowed the match to continue. I loved the fact that there were no swerves in this match and no none-finish as I was cautiously expected there to be.

Despite his effort to work on the knees and ankles of  Undertaker the Olympic gold medal winner could not make him tap out. Angle countered the Tombstone piledriver and the Last Ride into the Angle Lock, but “The Phenom” refused to tap out. You have to see for yourself how great some of these  sequences are.

It looked as if  Undertaker would be leaving No Way Out with the World Heavyweight Championship when he locked in his triangle chock on Angle, but Angle rolled through and got a quick three count before anyone even realized what had happened.

The dusty finish did little to nothing to affect my opinion of this match, as it made it look as if Angle escaped the lair of  Lucifer himself, unscathed. The look on the champion’s face after he realized he won supports this.

A few months later Kurt Angle asked for his release and got it. This match was really the last contest where we see a (some what) healthy Kurt Angle at his best in a WWE ring.


To me this was the pinnacle of WWE’s booking history. Everything in and around this match just clicked and fired on all the right cylinders.

This is without a doubt Undertaker’s greatest match of all time and in my opinion it is also the most well done Hell in a Cell match since the match’s creation.

This  stemmed from the outcome of the main event of SummerSlam 1997 we discussed earlier. After Michaels cost Undertaker his WWE Championship, he of course wanted revenge in the worst way and got Michaels in the first ever Hell in a Cell match at Bad Blood in October of 1997.

The future WWE legends had a mastery understanding of how to conduct a match and even in the uncharted waters of Hell in a Cell were able to put together one of the greatest wrestling matches I have ever seen.

The match set the bar high for future Hell in a Cell matches and in my opinion it has still not been topped even though it is over 15 years old.

Both men did some really revolutionary stuff in this match. Using the cage as a weapon and climbing on top of the cage was very taboo in the wrestling world at this time. 

The Undertaker and Shawn Michael’s match here was a really an important part of wrestling history also.

During the match when it looked like Undertaker was ready to put Michaels away, the lights went out and Kane walked to the ring for the first time and laid waste to his older brother. This set the stage for their match at Wrestlemania XVI which we talked about earlier.

Less than a month after this match Shawn Michaels faced Bret “The Hitman” Hart at Survivor Series in a match that would go down in wrestling history forever, but for all the wrong reasons.

Karma would catch up with “HBK” as a few months after that Shawn suffered an injury, ironically in a match with The Undertaker. The injury he suffered would (temporarily) ended his career, but also changed his life for the better.

Years later both men are now considered the most talented performers and biggest legends to ever step into a WWE ring.  Undertaker even got the honor of being the last man to ever wrestle with Shawn Michaels ending his career on a high note.

Their careers have been so similar and both men have been corner stones for the WWE, and will go down in history as two of the highest caliber performers of all time.

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