The Undertaker has wrestled plenty of unforgettable matches over the years, as well as some we’d rather forget. Which ones stood the test of time?
It still doesn’t feel right that The Undertaker is no longer an active member of the WWE roster. The legend wrestled for the company in four different decades before he finally hung up his hat and coat and drove off on his motorcycle into the night three years ago.
Over the years, the man known as the Conscience of the WWE has become a pop-culture phenomenon (he is, after all, The Phenom), becoming one of the most recognizable characters in sports, entertainment, television, video games, and comic books. He has quite simply done it all. And that made his retirement in 2020 an incredibly bittersweet one for his legions of fans – especially those who grew up watching him perform.
His final match was the Boneyard Match at WWE WrestleMania 36 against AJ Styles; a cinematic spectacle that entertained audiences around the world during the pandemic. It also turned back the clock and made up for some of the more questionable matches he had found himself in over the final few years of his career.
Speaking of the highs and lows of The Deadman’s career, let’s take this opportunity to reflect on some of his most iconic – and infamous – matches, and celebrate his legendary run.
The Undertaker vs. Mankind – King of the Ring 1998
Let’s start with what is probably the most infamous match of The Undertaker’s career. A renewal of his ’96 feud with Mankind saw the two mortal enemies meet inside Hell In A Cell at King of the Ring in 1998. It would be only the second ever Hell In A Cell match on pay-per-view and that was a fitting battleground for the final chapter of their storied feud. What neither men knew at the time was that they were about to make history.
The match hadn’t even started when Mankind challenged The Undertaker to come up to the roof of the cell. Just a few short moments later, it was Mick Foley who ended up falling all the way back down to the ground, having crashed through the announce table after ‘Taker forced him off the cell. The match should have ended there, but Foley climbed back up and came back for more – only to end up getting Chokeslammed through it.
The match is infamous for those two moments, but a bloody brawl ensued after that as the two rivals threw Chokeslams, Tombstones, and even thumbtacks at each other. It was The Undertaker who walked out victorious, but neither man would ever be the same. And history, well, that was well and truly made.
Verdict: BEST
The Undertaker vs. Triple H – WWE Super ShowDown 2018
There’s a strange irony in the fact that this list features a match between The Undertaker and Triple H on both the best and worst ends of it, but that goes to show you that sometimes history doesn’t need to be repeated. WWE didn’t get that memo and insisted that the two turn the clock back six years at Super ShowDown 2018 and repeat their “End of an Era” shtick in a rematch billed as the “Last Time Ever”.
They weren’t feuding. Neither one was competing full-time anymore. And their story had ended perfectly inside Hell In A Cell back in 2012. There was no need for this. Like at all. And yet, WWE made it happen, hoping to sell tickets and increase viewership for the major live event in Australia. Sure, that worked, but it didn’t make their actual confrontation a pleasant watch.
Look, it is what it is. These two legends were past their prime at this point, so they weren’t going for finesse and athleticism. Instead, it was just a bonkers brawl that made its way all over the arena and involved some sledgehammers, tables, and even Kane and Shawn Michaels. But that sweet, sweet WrestleMania chemistry they once had just wasn’t there. This was more like their earlier clashes in which they just didn’t click.
It wasn’t the worst match of either man’s career, but it was an unnecessary epilogue in a story that had been completed years prior to this, and it almost tainted that perfect ending.
Verdict: WORST
The Undertaker vs. Batista – WrestleMania 23 (2007)
When The Undertaker and Batista were told they weren’t getting the main event slot at WrestleMania 23, they decided to go out there and make WWE regret that decision. Somehow, someway, the two behemoths pulled it off, delivering a match so good it was deemed the Match of the Year when 2007 came to an end.
The pair’s clash inside Ford Field was for the World Heavyweight Championship and it had every right to be the main event given that Undertaker had won the Royal Rumble. It had no right, however, being as darn good as it was, because we were all caught off-guard by how incredible the pair’s chemistry was. For real, these two brought the house down with a hard-hitting brawl that told a great story, as The Phenom had to adapt to defeat the powerhouse Batista, who turned up to the event ready to win.
‘Taker was in the prime of his career, and this would be the beginning of an incredible string of matches for him. That shouldn’t have come as a surprise because he’s always been outstanding when paired with the right opponent; it’s just that no one thought Batista would be that perfect partner for him.
Their ’07 rivalry is one of the best of both men’s careers, but their WrestleMania 23 bout remains atop the mountain as their greatest collision.
Verdict: BEST
The Undertaker vs. Giant Gonzalez – WrestleMania IX (1993)
If this match was a movie and you wanted to know whether it had a post-credits scene, the answer would be yes, and it would be worth waiting for. The sequence at the end of the match, where The Undertaker rises after being knocked unconscious by a chloroform rag and takes the fight to the Giant Gonzalez, is easily the most entertaining part of the whole affair, as the audience screamed in excitement as The Phenom stood tall over his larger opponent.
However, the match leading up to that moment wasn’t exactly a crowd-pleaser. In fact, it once held the title of being the worst match of ‘Taker’s Streak for over two decades, and it’s disappointing DQ finish didn’t help it beat those allegations. Its biggest problem, however, was the fact that Gonzalez was limited in the ring, and Undertaker’s original Western Mortician gimmick meant that he could only respond by slowly stalking and striking his opponent.
This made a decent match virtually impossible, as ‘Taker couldn’t let loose on the giant in the same way that he did in his entertaining Last Man Standing match with The Great Khali over a decade later. The result is a slow, meandering match that never feels like the clash of the titans it was billed as.
But hey, the post-credits scene (and The Undertaker’s vulture entrance) is worth it!
Verdict: WORST
The Undertaker vs. Triple H – WrestleMania 28 (2012)
The Undertaker and Triple H are two of the biggest titans in WWE, and two of its most consistent workers. However, their in-ring chemistry hasn’t been the strongest over the years, with some of their earlier (and later) collisions being a little, well, rough. And yet, whenever the lights were on bright at WrestleMania, they defied the odds, producing three cracking showdowns at the Showcase of the Immortals.
Of the three of them, it was their Hell In A Cell match at WrestleMania 28 that shone the brightest. Billed as the “End of an Era” match, it saw the structure’s two greatest warriors do battle for supremacy with The Streak on the line. Adding to the drama was the fact that Shawn Michaels, Triple H’s best friend and the one man who came closest to ending The Streak, was the special guest referee.
On a night that saw John Cena and The Rock headline, it was this match that people were left talking about when the event came to an end. The storytelling between the two – Undertaker’s will to redeem himself after being unable to leave the arena on his own after their previous match, Triple H’s determination to become the one to end The Streak – it was all perfect, making for one heck of a compelling affair. Michaels’ involvement also upped the stakes, with that Sweet Chin Music into a Pedigree sequence (followed by ‘Taker kicking out at 2) being one of the greatest moments in WrestleMania history.
Another great sequence? Seeing the three titans of the Attitude Era embracing after their war was over. It was the perfect way for The Undertaker to mark going 20-0, and for the three of them to bid farewell to wrestling’s greatest era.
Verdict: BEST
The Undertaker vs. Giant Gonzalez – SummerSlam 1993
The ’90s really were a funny time for wrestling. While certain gimmicks from the early days of the WWE evolved with the time (like, well, The Undertaker of course), many of its elements did not. And the Rest In Peace match that really wasn’t anything other than an anything-goes match (with a black wreath for the loser) is one of them.
The ‘Taker’s bout with Giant Gonzalez at WrestleMania IX is quite infamous because it’s part of The Streak, but their rematch at SummerSlam 1993 is all-but-forgotten about. Maybe that’s for the best, as it doesn’t add anything of value to their story other than being a gimmicky way for The Deadman to end the feud by coming out on top. But the thing is that it wasn’t even all that gimmicky or fun. It’s just there, existing as a match with a gimmick attached to it while never really making use of that to entertain us.
Like their WrestleMania clash, it was the antics outside of the match that stole the show here, as Paul Bearer’s triumphant return (and subsequent run-in with Harvey Wippleman) was easily the most joyous moment of the whole thing. And that was very much needed after a rather joyless match that just saw The Undertaker being pushed and poked around the ring.
You can decide if it’s better or worse than the pair’s WrestleMania altercation but it really was essentially just more of the same.
Verdict: WORST
The Undertaker vs. CM Punk – WrestleMania 29 (2013)
Well, wasn’t this one a surprise?
We say that knowing full-well what these two talents are capable of. But the truth is that nobody expected The Undertaker and CM Punk to walk into WrestleMania 29 and steal the whole damn show out from under The Rock and John Cena (the second time ‘Taker did that in a row), but that’s exactly what happened.
Punk sought to end The Demon of Death Valley’s undefeated streak at WrestleMania, while The Undertaker sought vengeance for his opponent’s disrespectful actions after the death of Paul Bearer. It was an emotionally-charged war that saw the two men have incredible in-ring chemistry – something fans were happy to see after the pair’s disappointingly short bouts in 2009.
The Deadman’s sit-up inside the Anaconda Vice was an incredible moment, as was the GTS-into-a-Tombstone counter. These were just two of the spots that got a huge reaction from the audience, who were enthralled by every moment of this incredible encounter.
The Best In The World was defeated by the Greatest of All Time in an incredible match that proved the latter was still capable of classics, while also paying one last tribute to the late, great Paul Bearer on the Grandest Stage of them All.
Verdict: BEST
The Undertaker vs. Kane – Bragging Rights 2010
The Undertaker and Kane engaged in just about every spooky, unnerving, and frightful match stipulations throughout their storied rivalry, but it wouldn’t be until 2010 that they finally met in a Buried Alive match. Unfortunately, the result left many fans wishing that it had remained a dream match in our heads than a reality on the screen.
Of all the feuds the pair have been involved in, their 2010 renewal of their brotherly fires was undoubtedly the most disappointing. From a story standpoint, it was fine, but the action wasn’t able to match up to it, as ‘Taker was in rough shape due to nagging injuries and in desperate need of time off, and in 2010, Kane just wasn’t the right opponent to bring out the best in him.
Much of the match went down like you’d expect a Buried Alive match to go. There was some brawling, walking, attempted burying, and then repeat. But this one just lacked the flow needed to give the storyline the emotional weight it craved, so when the Nexus randomly showed up for no reason, we were all left thinking “what?”.
Decisions were made. None of them made sense. And it was never referenced ever again, as if it never happened. Probably for the best when you think about it.
Verdict: WORST
The Undertaker vs. Kurt Angle – No Way Out 2006
When we appreciate The Undertaker’s greatest ever matches, this is one that often gets forgotten about. We’re here to right that wrong today, because this is nothing short of a classic. In fact, we’d go so far as to say it might just be the greatest wresting match of The Phenom’s career.
‘Taker and Kurt Angle had surprising in-ring chemistry. A 2003 encounter on SmackDown already proved that, as the wrestling machine managed to draw out one of The Phenom’s best matches at a time when he wasn’t handing much of them out. So the idea of them meeting again when ‘Taker was in his physical prime should have been incredibly exciting. But here’s the thing, we didn’t know that The Deadman, who was 40 years old at this point, was heading into his physical prime. And, oh, did he show us.
Their World Heavyweight Championship match at No Way Out 2006 is nothing short of spectacular. A showcase of technique, ability, counters, submissions, power, and world-class wrestling, they found the perfect synergy early on, gifting us with a spectacle in which both men were the aggressors, both men were the favorites, and both men knew how to outdo their opponent at every turn.
This is the kind of wrestling match you dream of, and the fact that we could have had this at WrestleMania 22 (instead of ‘Taker’s clash with Mark Henry) makes it a bittersweet one. Yes, more people would give this match the flowers that it deserved if it took place at the Showcase of Immortals, but who knows if it would have been as perfect as this one if they had waited the month. Irrespective of that, their match at No Way Out is a stunner, and it’s time we showed it the appreciation it deserves.
Verdict: BEST
The Undertaker vs. Goldberg – WWE Super ShowDown 2019
What were they thinking?
Having learned nothing from the previous year, WWE continued to put The Undertaker in marquee matches against fellow legends, forcing him to work that much harder in the final few years of his career than he should have had to. And, believe us when we say he worked hard to make this match good.
It’s an odd thing to say for a contest that lasted less than 10 minutes, but the match with Goldberg at Super ShowDown 2019 was far longer than it needed to be. Goldberg isn’t known for long battles, and 2019 Undertaker looked far better in short bursts. But alas, somebody thought it would be a great idea to put two aging veterans out in the heat and have them wrestle a match that didn’t just consist of finisher spots (when that was really all it needed to be).
So much went wrong with this one in such a short space of time. Should we talk about how Goldberg’s Jackhammer almost dropped ‘Taker on his head? Or what about how Goldberg’s own head hit the mat during the Tombstone? Or maybe we should talk about the reverse Tombstone spot that always ended up being botched after 2015.
In fairness to The Undertaker, the match’s shortcomings were not on him and when he saw an opportunity to end it quickly before anymore damage was done, he took it. But he knew that continuing this match beyond the Tombstone was a mistake.
Verdict: WORST
The Undertaker vs. Shawn Michaels – Badd Blood: In Your House (1997)
Rarely is a trilogy of anything so good that you could call any of its installments its best, but that is indeed the case with the legendary battles between Shawn Michaels and The Undertaker. The pair have faced off more than three times and every one of those other installments were incredible, but their three most famous outings are among the greatest showdowns in WWE history.
First up, we have their legendary encounter at Badd Blood: In Your House back in 1997. Yes, we’re talking about the very first Hell In A Cell match – a match that also saw the legendary debut of The Undertaker’s “brother” Kane, who was single-handedly responsible for Michaels scoring the victory.
There was a lot happening here that you would be forgiven for forgetting the sheer quality of the wrestling, but we’re not about to let you do that. This was a very different affair from the one the two men would take on years later as respected veterans; it was brutal, bloody, and hard-to-watch at times, as the intimidating Undertaker sought revenge on the arrogant Michaels for costing him the WWE championship. ‘Taker had all the time in the world to stalk his prey inside the structure, and Michaels had nowhere to run.
They told a perfect story, throwing in some absolutely amazing action while doing so. The visual of Michaels losing his grip on the cell and falling down through the announce table is one that will live in infamy forever, highlighting the dangers of Hell In A Cell and showcasing what these two were capable of in any environment. And it’s almost as legendary as the sight of Kane ripping the door off its hinges.
Everything came together on this night, and the resulting match was glorious.
Verdict: BEST
The Undertaker vs. Brock Lesnar – WrestleMania XXX (2014)
I don’t know what’s more disappointing: The fact that The Streak had to end at all, or the fact that it ended after this mess of a match.
The Undertaker got concussed early on in the 2014 game-changer and that made the whole thing an unpleasant watch before that final bell rung. The man himself has rewatched the match and still can’t pinpoint when exactly it happened, and neither can we. But it did happen, because the normally dominant Deadman had a glassy look in his eyes for the majority of the match. He was unsure of himself, sluggish in his movements, and completely zoned out. And that meant that he couldn’t carry Lesnar, who was still working out what kind of matches were his bread and butter, to a good match.
This was just a case of bad luck. While the strategy of the match never seemed right, as it appeared that they were going for WrestleMania ‘Taker battling Lesnar in a wrestling match, instead of just having the two brawl viciously, the match’s failure can be attributed to The Phenom’s injury. The fact that he managed to pull off two sensational showdowns with The Beast the very next year is proof that he could still go. It just didn’t come together on the night.
The Streak, and the infamous moment that it ended, deserved better than this.
Verdict: WORST
The Undertaker vs. Shawn Michaels – WrestleMania 26 (2010)
The Undertaker and Shawn Michaels’ collision at WrestleMania 25 was absolute perfection, but there was one mistake that WWE made that night and it was not making that match the main event. They sought to put things right the very next year when we all got the most anticipated sequel in WrestleMania history, as the two legends collided one more time. To raise the stakes, The Heartbreak Kid put his legendary career on the line.
The Streak vs. Career match is a worthy successor to their previous classic. It’s almost as perfect of a wrestling match, with some stunning spots including a Tombstone on the outside, a Sweet Chin Music onto and Moonsault through the announce table, and so many near-falls. The area where this one excels, though, is its storytelling, as it finally felt like Michaels had the edge, that he could become the one to end The Streak and that he would live to fight another day. And then he made The Undertaker mad.
The “stay down!” and slap sequence into the jumping Tombstone finish was the perfect way to end this classic. Michaels (and his career) was going out swinging, while The Phenom was reluctantly burying HBK’s legendary career. A compelling end to a fantastic story that these two icons told in the ring that night.
Michaels and ‘Taker gave us the greatest main event in WrestleMania history, but the only thing preventing this one from being the event’s all-time greatest bout was, well, themselves…
Verdict: BEST
The Undertaker vs. Roman Reigns – WrestleMania 33 (2017)
Roman Reigns and The Undertaker are two people capable of amazing matches with the right opponent. But neither one was right for the other, so when they collided in the main event of WrestleMania 33, expectations were already pretty low – especially because WWE’s insistence on pushing Reigns to the forefront of everything made him the likely winner before the match even began.
Even with those low expectations, the match was a trainwreck. It started out okay, but things quickly fell apart as ‘Taker looked noticeably winded, and Reigns wasn’t the opponent to carry him to a stronger performance. So the decision to put these two out there in the main event match for a ridiculous 23 minutes was just baffling. And believe me when I say, it felt every bit of that 23-minute runtime.
With ‘Taker being sluggish for most of the match (and preparing for hip surgery shortly afterwards), he shouldn’t have been in the ring that year. Or, at the very least, he could have shown up, squashed someone and went home. He can always put on a show with the right dance partner, but this was a miscalculation on all sides, making Reigns’ predictable victory that much more painful because it came after this struggle of a match.
Verdict: WORST
The Undertaker vs. Shawn Michaels – WrestleMania 25 (2009)
You knew this one was coming, didn’t you? Of course, the greatest match of The Undertaker’s career was his unforgettable showdown with Shawn Michaels at WrestleMania 25. There was just no other choice!
It was only right that WrestleMania’s two greatest performers fought one another on its 25th anniversary, but what Undertaker and Michaels went out there and did that night ensured that audiences will be talking about it for the next 25 years. Heck, we’re 14 years of that quarter-century down and we’re still raving about it.
The pair’s chemistry was well-documented at that point; they had already produced phenomenal matches in the ’90s, but could they do it again over a decade later? The answer was no; they could do better. Not only did those two 40+ athletes outperform everyone else on the roster that night, they overperformed in every imaginable way, producing what is perhaps the greatest match in WWE history.
From both extraordinary Tombstone spots to the sheer look of exhaustion and shock on The Phenom’s face after Michaels’ kickout, this was a masterclass in both wrestling action and storytelling – and not even that near-disastrous over-the-rope spot could take away from that.
This was nothing short of perfection.
Verdict: BEST
Which of The Undertaker’s countless matches was your favorite? Do you have a best and worst?