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…
HONORABLE MENTION: THE UNDERTAKER VS. RANDY ORTON (WRESTLEMANIA 21)
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.
- 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. THE UNDERTAKER VS. BATISTA (BACKLASH 2007)
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.
9. THE UNDERTAKER VS. JEFF HARDY (WWE RAW; JULY 2002)
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.
8. THE UNDERTAKER VS. KANE (WRESTLEMANIA XIV)
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.
7. THE UNDERTAKER VS. EDGE (WRESTLEMANIA XXIV)
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.
6. THE UNDERTAKER VS. BRET HART (SUMMERSLAM 1997)
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…
5. THE UNDERTAKER VS. TRIPLE H (WRESTLEMANIA XXVIII)
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.
4. THE UNDERTAKER VS. THE ROCK VS. KURT ANGLE (VENGEANCE 2002)
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.
3. THE UNDERTAKER VS. SHAWN MICHAELS (WRESTLEMANIA XXV)
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.
2. THE UNDERTAKER VS. KURT ANGLE (NO WAY OUT 2006)
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.
1. THE UNDERTAKER VS. SHAWN MICHAELS (BAD BLOOD 1997)
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.