For over two decades, one man has become synonymous with WrestleMania, and despite what he might tell you, it’s not Shawn Michaels. No, that man is The Undertaker, whose undefeated Streak on the grandest stage of them all reached a startling 21 straight victories before being broken. Over his lengthy career, we’ve seen a variety of opponents try to take down the Dead Man, and except for one, they’ve all failed. Along the way, we’ve seen some of the best, and some of the absolute worst, matches in WrestleMania history. And now, we’ve ranked every single one of the Undertaker’s matches, in the definitive guide to the most successful wrestler in WrestleMania history.
24. Giant Gonzalez, WrestleMania IX
This, of course, is one of the matches that puts WrestleMania IX among the front-runners for “Worst WrestleMania Of All Time”. If you don’t remember who Giant Gonzalez is, count yourself lucky, because he could best be described as “a less mobile Great Khali”. And we’re talking about the later version of Khali, after his knees exploded and he couldn’t take bumps anymore. Plus, for your viewing pleasure, Gonzalez wore a full-length bodysuit covered in airbrushed muscles and tufts of hair. Just looking at Gonzalez is one of the most disturbing images in WWE history, let alone being forced to watch him wrestle. He was so large and immobile that Undertaker was unable to lift him and hit his Tombstone finisher, which is probably why WWE went with a ridiculous DQ finish where Gonzalez smothers Undertaker with an ether-soaked rag. Of course, that meant that Undertaker actually won the match, continuing what would eventually become The Streak, but if not for that technicality, The Streak could have been over before it really began.
23. The Big Boss Man, WrestleMania XV
This is not so much a “forgotten” Hell in a Cell match as it is one that WWE wishes everyone would forget (and yet, somehow not the worst Cell-related match the Boss Man would be part of, that being the infamous Kennel in a Cell). Setting aside the entire Attitude Era nonsense that was The Corporation and the Ministry of Darkness, two heel factions, fighting with each other while also fighting “Stone Cold” Steve Austin, putting this match inside Hell in a Cell, at the time, created certain expectations for insanity that a wrestler like Boss Man, well past his prime at this point, was never going to be able to fulfill. The match is a boring brawl that also suffers from the fact that WWE hadn’t quite perfected the design of the Cell in order to allow people to actually see what was going on very clearly. Actually, that might have been a blessing in this case. In the end, and in a moment that WWE has worked furiously to scrub from history, Undertaker defeated Boss Man and then had his Brood minions rappel from the ceiling and literally hang Boss Man from the Cell by his neck. Fortunately, Boss Man’s status was later upgraded from “dead” to “alive”, but not before WWE had another in a long list of needlessly disturbing imagery that came out of the Attitude Era.
22. King Kong Bundy, WrestleMania XI
Bundy was one of the most underrated big men in wrestling during the 80s and early 90’s, and was even in the main event of WrestleMania 2, facing Hulk Hogan inside a steel cage. But by WrestleMania XI, his stock was pretty low, as he continued to gain weight and lose mobility in large amounts. He still had some credibility as a heel, however, and was placed in Ted DiBiase’s Million Dollar Corporation (which ended up being one of the most ineffective heel stables in wrestling, but the intent was there). DiBiase’s team had kicked off what would become a year-long story line involving The Undertaker, with IRS “repossessing” his urn at the 1995 Royal Rumble, thanks to a surprise attack by Bundy. Undertaker would eventually work his way through most of the Corporation in an effort to reclaim his urn (which was eventually melted down into gold chains, because of course it was), finally regaining it from King Mabel in December. Thanks to his ambush, Bundy became the first man on Undertaker’s hit list, and the two faced off at WrestleMania in what was an incredibly slow and plodding match enjoyed only by die-hard Undertaker fans who thought he might actually succeed in getting his urn back so easily.
21. Big Show and A-Train, WrestleMania XIX
This was a mess on top of another mess, which turned into a six car pileup on the freeway. WWE had signed massive Australian wrestler Nathan Jones, who had size and a great character on his side, but almost no wrestling ability at all. Originally, the plan was for Jones to face The Undertaker at WrestleMania, but once it became clear that match might end up even worse than Taker’s bout with Giant Gonzalez, plans changed to Jones becoming The Undertaker’s protege, and they were set up to face The Big Show and A-Train (you might also know him as Albert, Tensai, and a few other terrible gimmicks). Unfortunately, in the weeks leading up to WrestleMania it became clear to WWE that Jones wasn’t going to be able to successfully perform in that much smaller role, and they began to waffle on whether to even have him compete in the match. In the end, they had Jones taken out backstage before the match, forcing The Undertaker to wrestle a handicap match against two big, slow wrestlers. The result was predictable, and since The Streak was quickly becoming a legitimate thing, The Undertaker still managed to defeat both men at once.
20. Jimmy Snuka, WrestleMania VII
Once one of the biggest stars in the industry, by 1991, Jimmy “Superfly” Snuka was clearly in decline as a wrestler. The Undertaker, on the other hand, was one of the hottest young stars in the industry since debuting a few months earlier at the Royal Rumble, and this match was set up to give him a big, recognizable star to defeat easily, thus making The Undertaker look like an even bigger deal. Yes, WWE actually used to do that instead of having every single star from previous eras portrayed as still being better than their new, younger stars. But we digress. Frankly, this was a squash match that only lasted a few minutes, and only really exists as a trivia question about who the first Superstar to lose to the Undertaker at WrestleMania was. However, at least it was fairly inoffensive, unlike some of the matches that appear below it on this list.
19. Jake Roberts, WrestleMania VIII
We continue our tour through the mostly unmemorable early matches of the Streak with this bout against Jake “The Snake” Roberts, the feud which actually turned The Undertaker into a good guy for the first time. Roberts, as everyone likely knows, was one hell of a professional wrestler with a great mind for the business, who was unfortunately sidetracked by substance abuse issues for most of his career. At this point, he was basically on his way out of WWE, and would stay gone for several years before returning in 1996 to make one last-ditch effort at saving his career (which proved to be futile). Much like Snuka, this was a match that served the purpose of growing what would become the legend of The Undertaker, nearly effortlessly defeating one of the company’s former biggest stars, this time to the cheers of the audience, who had started to get behind the implacable and seemingly indestructible Dead Man.
18. Mark Henry, WrestleMania 22
It’s probably mean to say it, but over his near two-decade career in WWE, Mark Henry was only really good for about a year near the end, when he was doing the Hall of Pain gimmick and sending people to the hospital. This match with The Undertaker, unfortunately, was not during that period, and although Henry evolved into a decent big man over his career, he was far closer to Undertaker’s older WrestleMania opponents in terms of mobility and speed than the ones he began facing in the latter half of the Streak. To cover up for Henry’s deficiencies, this was actually a Casket Match, because for some reason, people are more willing to accept a slower match if it includes some sort of gimmick that allows the wrestlers to brawl around ringside and use objects as weapons. That’s not a judgment, just an observation. The good news is, Undertaker was pretty much about to hit his peak as a wrestler, and began doing things like his ridiculous dive over the top rope to the floor, which always impresses the crowd (possibly because it’s incredibly impressive). The match still isn’t very good, unfortunately, but not as bad as it could have been had the same two wrestlers met up a few years earlier.
17. Sid, WrestleMania 13
WrestleMania 13 is a one match show, and it’s definitely not this match. While not the worst match involving Sid to ever take place, it’s definitely not good, and it happens to take place at the end of a long, dull Pay Per View with only one real bright spot in the Bret Hart-Steve Austin match that changed wrestling forever. This is also the match that gave us the urban legend about Sid pooping himself in the ring, and while it’s apparently true that Sid has done such a thing in the past, it has been denied several times from several different sources that it happened here. So it doesn’t even have that interesting bit of trivia going for it! Technically, this was not the Undertaker’s first WWE Title reign (his first, which is often forgotten, was a two-day reign in 1991 that ended with the title vacated and up for grabs in the Royal Rumble), but it was the first time that it felt like he was being given a real shot at the top guy in the company, after being one of its most popular acts for so long.
16. Shane McMahon, Wrestlemania 32
WWE literally wrote themselves into a corner with this feud. Due to a ridiculous number of injuries in the months leading up to WrestleMania, they found themselves stuck without a marquee opponent for The Undertaker at what was supposed to be the biggest Mania in history. In a shocking surprise, they brought back Shane McMahon, who hadn’t been seen in WWE in roughly seven years, and set him up to oppose his father by demanding control over Raw. Vince responded by putting Shane in a Hell in the Cell match with the Undertaker, telling Shane that if he won, he could have the control he sought. However, Vince also threatened The Undertaker (who had no real reason to want to fight Shane in the first place), that if he couldn’t win it would be his last WrestleMania. Trapped between promising real change that fans wanted and the end of the Undertaker, they had Taker win the match, after Shane did the expected crazy stunt and jumped off the top of the Cell. The rest of the match was inoffensive, if you don’t mind watching Shane McMahon power out of every Undertaker finish, but the head-scratchingly insane booking of the match relegates it to the lower half of the list.
15. Kane, WrestleMania XX
Ever since The Undertaker became what is largely referred to as “BikerTaker” during the Attitude Era, speculation had run rampant about when he would go back to his original gimmick. We’re not kidding, it came up literally every time he disappeared from TV for a few weeks, and before any Pay Per View where he had a big match. Finally, at the twentieth WrestleMania, it was pretty clear that he would, in fact, be coming back as the Dead Man, facing his greatest nemesis Kane, who had buried him alive at Survivor Series. This match appears so high on the list because the sheer level of hype people had for the return of the zombie Undertaker gimmick was incredible at the time. WWE knew this, and made sure that he never appeared in the weeks leading up to WrestleMania, not even in the graphics promoting the match! Then, when the lights went off and the music started, the goosebumps started rising, and it was like he never left. The match itself was less a match than it was Kane screaming that Undertaker couldn’t possibly be real, followed by Taker quickly destroying Kane with his arsenal of signature moves, but as WrestleMania moments go, there are few bigger.
14. Brock Lesnar, WrestleMania XXX
So, obviously, this is the match that ended the Streak, and whatever mistakes WWE made afterwards, it’s hard to argue that Brock Lesnar is one of a very short list of people who could believably beat The Undertaker at WrestleMania. It will almost certainly go down as one of the most shocking moments in wrestling history, because people still can’t believe it actually happened. Unfortunately, the match is remembered for a lot of other reasons, most notably that The Undertaker suffered a massive concussion early on, and the match itself ended up being fairly bad as Lesnar tried to walk a clearly woozy Undertaker through what ended up being a nearly thirty minute-long affair. Clearly the intent going in had been to make the Streak-ending match suitably epic, but the injury basically ruined all those plans, and fans were left with a bitter taste in their mouths, because not only had Taker lost, he’d lost in a pretty bad match that seemed ill-suited for such a massive event. At the time, many figured that this would be Undertaker’s last match, both due to the Streak ending and because he was so damaged as a result that he ended up hospitalized. Of course, that turned out to not be the case…
13. Bray Wyatt, WrestleMania 31
This match wasn’t necessarily a bad match, but it was frustrating for wrestling fans for several reasons. Bray Wyatt had been in WWE for a while at this point, and was still lacking that big win that many thought could turn him into a huge factor as a heel for years to come. His aura as a powerful mystical figure was also slightly damaged at this point due to John Cena destroying him in a feud the year before, but many theorized that, with no Streak left to defend, perhaps WWE might be setting Bray up to defeat The Undertaker and assume his mantle as WWE’s resident scary supernatural guy. That actually would probably have been a decent plan, but instead, the two Superstars wrestled a basic match, and in a massive anti-climax, The Undertaker cleanly defeated Bray Wyatt. This upset several people, who couldn’t understand why WWE would decide to feed one of its young and talented Superstars to a wrestler that only appeared a handful of times, maximum, every year, and who no longer had any stakes in winning at WrestleMania. It was at this point that more people began questioning why WWE had even bothered ending the Streak in the first place, if they were still going to lean on The Undertaker’s WrestleMania wins as an attraction.
12. Kane, WrestleMania XIV
The culmination of the events that led to Kane’s debut at Badd Blood gave this match an incredible aura, helped along by the crowd being white hot for WrestleMania and the rise of the Austin Era which would cap off the evening. Ever since his younger brother had made his shocking entrance into WWE, Undertaker had looked weaker than he had in a long time. Rather than facing his opponent head-on, he avoided fights with his brother, refusing to fight his long-lost family member. At one point, it seemed like an alliance was formed between the brothers, but that was quickly dashed when Kane locked Undertaker in a casket at the Royal Rumble and lit it on fire. The storytelling that led up to this match was just excellent, and Kane’s seeming indestructibility gave true doubt that Undertaker would be able to handle his brother. The match, ultimately, was good, but not great, helped by a good crowd and a well-crafted story that seemed tailor-made for Undertaker to dramatically defeat his brother. Also, it gets bonus point for being the very first time that Kane beat up Pete Rose at WrestleMania.
11. Diesel, WrestleMania XII
Here we have the first time that people suspected that The Undertaker, famed for wrestling matches in a slow, methodical style that fit with his gimmick, might actually be a pretty good wrestler. It definitely helped that Kevin Nash was still relatively young, healthy and motivated at this point in his career (mostly because he was already planning to jump to WCW, but whatever worked), and the result is a match that might have stolen the show at any Pay Per View that wasn’t being headlined by a 60-minute Iron Man match between two of the greatest wrestlers in the world at the point. Unfortunately, this match often gets forgotten when talking about Undertaker’s best WrestleMania matches, but for a long while, before he reinvented himself and got to face some actually good wrestlers instead of a line of aging or immobile wrestlers, this was probably his best Mania match.
10. Triple H, WrestleMania XXVII
So, after Shawn Michaels tried and failed on two consecutive occasions to end the Streak, costing HBK his career but leaving wrestling fans with two all-time classic matches to remember him by, his buddy Triple H apparently decided that he wanted some of that love and respect for having great matches with The Undertaker, too. At this point, ending The Streak was reaching impossible levels, as Taker had set down some of the biggest names, including Michaels, in the last few years. But when it’s Triple H, you always worry that today might be the day he decides that he has to win, consequences be damned. At any rate, while it is a well-wrestled match, technically, it suffers from a few things. First of all, it was never going to be able to follow the HBK-Taker series, and it was probably laughable to try. Secondly, it is a problem in some big Triple H matches that he will decide that he wants the match to be “epic”, and to him, that means a match full of of big spots, including one very early in the match in order to make the audience believe that both men are already badly hurt, followed by a minute or so of everyone lying on the mat trying to recover. If there was one thing that we didn’t particularly care for in this match, which many people still enjoy, it would be that. The match was good, but very slow at times, and if that makes it appear suitably epic in your eyes, then more power to you.
9. CM Punk, WrestleMania XXIX
Some might suggest we placed Punk’s match above Triple H’s out of spite, and maybe at a certain level they’re right. But to be fair, it’s still ranked below two other Triple H matches. Any match with CM Punk at this point in his career was going to be pretty good, but it’s very hard for us (and for Punk, allegedly) to see this match as anything more than a consolation prize for the guy who had the longest WWE Title reign of the modern era, only to have it end because WWE wanted the Rock-Cena re-match to be for the WWE Title. If we had to guess, this is probably the point where Punk started getting more than a little fed up with his treatment, leading to his departure just under a year later. The match itself is good, and both men worked hard to try and build up an interesting feud going into the Pay Per View, which became even more difficult when Undertaker’s former manager, Paul Bearer, passed away just as the build to WrestleMania was getting underway. This is another match that will get glossed over when The Undertaker’s legacy is remembered, both because of CM Punk’s battles with WWE and because it really was forgettable, but the quality of the match should not be ignored.
8. Triple H, WrestleMania XXVIII
The final (for now) clash between Triple H and The Undertaker was billed as an “End of an Era” match (although both men would continue to wrestle for years afterwards, leading many to wonder exactly what era had ended that night), and took place inside Hell in a Cell, with Shawn Michaels as a special guest referee. As opposed to their match the previous year, this was one where fans expected to see an “epic” match, and a certain amount of laying on the mat in pain is seen as an acceptable part of the match structure. More importantly, by adding HBK to that match and giving him a moral dilemma between helping his best friend and not wanting anyone to accomplish what he was unable to do, it added dramatic tension to the match that Shawn played out after every big spot left both wrestlers down. Having something happening while the actual wrestling action was absent was the ingredient that they’d been missing the year prior, and rendered this match suitably epic.
7. Ric Flair, WrestleMania X8
It was about this point that people started to notice that The Undertaker never lost at WrestleMania. He was still a relatively modest 9-0 (in terms of The Streak itself, becaue 9-0 was still a far better record than anyone else at WrestleMania), and for the tenth match, WWE turned to one of the true legends of the industry, Ric Flair, who had recently returned to WWE and declared himself part-owner, leading up to a brand split that would take place in the weeks immediately following WrestleMania. Flair had also shown that he still had some good wrestling left in him, after fighting Vince McMahon in a pretty good Street Fight at the Royal Rumble. So, when The Undertaker tried to cross the new boss, Flair responded the only way he knew how, by challenging Taker to a match at WrestleMania. This is another Streak match that really doesn’t get enough credit, because like most of the rest of the card, it was largely forgotten due to the epic Rock-Hogan match. But with both Flair and Taker established, wily veterans, they managed to put on one heck of a match considering the advanced age of Flair, which also featured a crowd-popping run-in by Flair’s best friend, Arn Anderson, hitting one of his patented spinebusters to create an incredibly close near-fall. After Undertaker defeated Flair, he visibly counted to ten on his fingers, marking the point where WWE, and people in general, began to really pay attention to The Streak.
6. Edge, WrestleMania XXIV
For the second straight year, The Undertaker found himself in a match for a World title, this time facing off against the Rated R Superstar, who had begun to dominate the Smackdown brand thanks to his alliance with GM Vickie Guerrero. As one of the biggest stars on that brand, and a respected veteran, Undertaker took it upon himself to stand up to Edge, winning an Elimination Chamber match to earn his title shot. Despite arguably larger matches happening elsewhere on the WrestleMania card (including what would turn out to be Ric Flair’s final WWE match), this match was the main event of the show. Edge and The Undertaker showed an uncanny chemistry in this match, which would carry over into an extended feud that lasted much of 2008 and probably helped cement Edge as one of WWE’s biggest stars in that era. The match was a well-paced, excellently wrestled endeavor that managed to get a crowd that had already been emotionally drained over a very long show worked back into a frenzy for the finish. It also featured one of the inadvertently funniest images in WrestleMania history, as referee Charles Robinson, who is not a tall man, was forced to sprint down an incredibly long entrance ramp to make the final three count after the original referee was knocked out.
5. Randy Orton, WrestleMania 21
With The Streak well on its way to becoming legendary, it was probably inevitable that the man who called himself the Legend Killer who take his shot at ending it. Fresh off a massively failed face turn that saw his all-but-guaranteed match for the World Heavyweight Title at WrestleMania taken away and given to his former stablemate Batista, Randy Orton went a little crazy and reverted to his diabolically evil persona. He already had a list of Legends that he’d defeated, and was seen as someone who WWE had definite big plans with for the future, so it was reasonable to believe that Orton might have a chance where others had failed. In fact, rumors persist that Orton was, at one point, supposed to win this match. However, it turned out to be for the best that Orton did not break The Streak, as the match aggravated a serious shoulder injury he had suffered (something which would develop into a chronic condition for Orton), and Orton was forced onto the injury list almost immediately after WrestleMania, not returning for several months. The match itself showed off Orton’s undeniable talent, even at a young age, as he and Taker put on an excellent match that actually had people believing that Orton could win it all.
4. Triple H, WrestleMania X7
In his first WrestleMania under his new gimmick as a motorcycle riding Dead Man, at what would turn out to be the biggest WrestleMania of all time in terms of critical reception, it was necessary for The Undertaker to have a high-profile opponent. Fortunately, after plans to have him face his former partner Shawn Michaels fell through, Triple H was readily available. The two quickly built an intense feud on the basis of mutual dislike, and when they entered for their match at WrestleMania, both seemed determined to have a match that might possibly outshine the highly anticipated Rock-Austin main event, which would follow them. In the end, they fell short of this goal, but still put on a crazy brawl that spilled all over the arena and had the crowd excited the entire way through. It even included Triple H taking a relatively big (though obviously cushioned) fall off a camera tower, a rarity in a match involving both men, who were not known for leaving their feet, let alone falling off things.
3. Batista, WrestleMania 23
Batista, like Edge, is another wrestler who seemed to bring out the very best in The Undertaker, and the results would be some of the best big man matches of that era of wrestling. Headed into this match at WrestleMania, which was for the World Heavyweight Championship, Batista’s career had been sliding from the peaks of earlier years. His in-ring style had stagnated, and he seemed less and less motivated during a lengthy feud with King Booker than spanned most of the summer and fall. However, The Undertaker had won the Royal Rumble in impressive fashion, putting on a show with Shawn Michaels when they were the final two competitors that suggested he was reaching the peak of his wrestling abilities. With lowered expectations heading into their Mania match, Batista and Taker tore into each other in what turned out to be a pretty great match and pretty much resuscitated Batista’s ailing main event career.
2. Shawn Michaels, WrestleMania 26
Well, at this point, you’re asking us to choose between our children, because the two matches between Shawn Michaels and The Undertaker were among the greatest in either man’s legendary career, and are certainly two of the best WrestleMania matches of all time. This match had a bigger emotional weight that the first one, because HBK put his career on the line, but by the same token, it also had a certain sense of inevitability about it, as it was incredibly unlikely that Michaels would succeed on his second attempt, and there were rumors of his impending retirement well before the match was even signed. The specter of Shawn’s imminent doom didn’t stop them from having a spectacular match, with both men throwing absolutely everything at each other, especially Michaels (who was likely comforted by the knowledge that it as hist last match). Unlike the first match, WWE also made the intelligent decision to have them as the main event of the evening, making it the perfect emotional finish to an otherwise fairly forgettable WrestleMania.
1. Shawn Michaels, WrestleMania 25
In our opinion, by the slimmest of margins, this is the better match. It’s likely that the fact that this match doesn’t have the same inevitability as the second one does that tips the balance. With nothing on the line other than pride and The Streak, it was conceivable that Michaels might actually be the man who could take down the Undertaker. In addition, there was the unknown possibilities of what the match might contain, as Shawn and Taker had not faced each other in over a decade. While the second match builds on the foundation established here, it was an incredible foundation and a classic match in its own right, without the added sadness that came from watching a legendary career end before our eyes. We don’t blame you for picking the second match over this one, but in our eyes, this was the best match that The Undertaker ever had at WrestleMania, and we can’t imagine there will be many who argue.