Undertaker: Ranking Every WWE WrestleMania Match of the Deadman's Career
When WWE fans think of WrestleMania, they inevitably think of the legendary Undertaker.
Even now that the streak has come to an end, The Deadman is a true icon of The Showcase of the Immortals. Over the past decade, showcase matches against Undertaker have become just as important as the world title defences on the show.
Undertaker is one of the most distinct characters in WWE and certainly one of its standout big-match performers. As such, he's developed a large back catalogue of amazing WrestleMania performances.
This year's clash with Shane McMahon will undoubtedly be compared to these bouts, and it will take a truly special encounter inside Hell in a Cell to climb up the ranks of this list of WrestleMania masterclasses.
23. Giant Gonzalez vs. Undertaker at WrestleMania IX
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While competition at the top of this list is very fierce, there's no doubt that Undertaker's match against Giant Gonzalez ranks as the worst of his WrestleMania output.
The Phenom was not the seasoned ring veteran he would later grow into at this point, which made it very difficult for him to wring anything enjoyable out of his opponent.
Giant Gonzalez was a truly awful wrestler, his lone saving grace being that he was very big and tall. His attempts to play up Undertaker's offence seemed well-intentioned, but the cartoonish nature of his movements actively detracted from the bout.
Things went from bad to worse when Gonzalez whipped out a rag doused in chloroform, prompting the lone DQ win of Undertaker's streak. Things only got sillier when medical personnel hit the scene, as the setting of Caesar's Palace meant that they were decked out in Roman garb.
This match was the very definition of a dud.
22. King Kong Bundy vs. Undertaker at WrestleMania XI
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The biggest problem with Undertaker's 1995 match against King Kong Bundy was how inconsequential the bout felt. For a bout on the biggest card of the year, it was largely preoccupied with extending a storyline rather than providing any closure.
The narrative in play centered on Undertaker's urn, which had been stolen by Ted DiBiase as a means of clipping the wings of The Phenom.
DiBiase was an excellent presence, and the hijinks with the urn were enjoyable enough, if dated. The in-ring component was simple but well-executed, but ultimately there was nothing about this encounter that warranted a spot on WrestleMania—much less a viewing 20 years after the fact.
21. The Big Bossman vs. Undertaker at WrestleMania XV
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Here's hoping that when Undertaker enters Hell in a Cell at this year's WrestleMania, the results are closer to his encounter with Triple H at the 2012 edition of the show than this overwrought mess from 1999.
Outside of the visual of the structure itself, there was really no substance to this match. It's possible that this wasn't entirely the fault of the competitors—a pair of handcuffs used to restrain Undertaker broke, and the confusion that followed suggested his imprisonment might have played a bigger role otherwise.
The post-match events, in which The Brood made an appearance from the rafters to help suspend the Big Bossman by a noose, was clearly what the match is building towards, but it fell flat.
All in all, there wasn't enough to sink your teeth into here.
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20. Big Show and A-Train vs. Undertaker at WrestleMania XIX
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The lone multi-man match from Undertaker's WrestleMania output was a rather tepid affair featuring the Big Show and A-Train—aka Albert, aka Lord Tensai, aka Giant Bernard.
This bout became a handicap match after Undertaker's teammate Nathan Jones was taken out via backstage attack. The deck was firmly stacked against The Phenom, who was pitched as an ultra-patriotic fan favourite, dedicating the bout to his nephew serving in the military.
Things proceeded much as you would expect; after a hot start taking on both men, the numbers game eventually caught up with The Deadman.
A-Train showed some of the quality that would later bring him plenty of success wrestling in Japan, but things weren't so slick when Big Show was in the ring. At one point, Undertaker tried a neat armbar counter to his chokeslam, but the big man's execution really let down the spot.
The biggest problem with this bout was its brain-dead conclusion: Jones hit the ring—apparently having made a miraculous recovery—and evened the odds for Undertaker. While the action beforehand wasn't much to write home about, this trite conclusion really brought things to an end on a sour note.
19. Mark Henry vs. Undertaker at WrestleMania 22
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Despite taking place in the 2000s, this bout had much more in common with the earliest Undertaker appearances at WrestleMania, pitting him against the monster of the week. Unfortunately, a match that could have been a fun clash of the titans was handicapped by its Casket Match stipulation.
Slow-paced action was punctuated by forced use of the casket as a prop, most of which threatened to veer into slapstick comedy. Both men jockeyed for position while inside the oversized coffin, which was a very silly sight.
The casket was used to its greatest advantage when Undertaker performed one of his trademark outside dives, clearing it handily in the process. Other high points included both men hitting thunderous versions of their patented finishers. However, those rare bright spots couldn't save this from being a mundane WrestleMania outing.
18. Jimmy Snuka vs. Undertaker at WrestleMania VII
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Undertaker's shortest WrestleMania match came at his first appearance on the show. This encounter with Jimmy Snuka was a squash, but a largely well-executed one.
The Phenom was still finding his feet, both in terms of his character and the in-ring component of his act. That said, Paul Bearer had already hit the ground running in his role and added a great deal to proceedings.
What Undertaker lacked in technique he made up for in sheer vigour—an early iteration of his trademark flying clothesline was a good example.
A spot where Snuka gets hung up on the ropes was very entertaining, and it looked set to be followed up by an interesting finish, which didn't quite go as intended. Despite the rough edges on show, there was plenty of promise in this inaugural WrestleMania showing for The Deadman.
17. Kane vs. Undertaker at WrestleMania XX
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The 20th edition of WrestleMania saw Undertaker return to his Deadman persona, dropping the biker aesthetic of The American Badass. A clash with half-brother Kane sounded like the perfect match for the job, but his persona here wasn't quite the right fit.
Far from being The Big Red Monster, Kane played the coward. He was never really made out to be much of a threat to Undertaker—in fact, this was more of a showcase for The Phenom than a competitive showdown between the two.
The crowd provided a lively response to Undertaker's signature moves, but for the most part there was nothing much for them to get too excited about.
Characters as iconic as Undertaker and Kane deserved a much better WrestleMania encounter than this one—and, thankfully, they did have a better bout several years earlier.
16. Bray Wyatt vs. Undertaker at WrestleMania 31
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The biggest problem with this bout from 2015 is that it couldn't decide whether to focus on rehabbing Undertaker after the end of The Streak or showcase a clash between two characters tinged with the supernatural.
The New Face of Fear made the most of his opportunity to take The Deadman down a peg, providing plenty of energy that made for some interesting shifts in pace. His offence was consistently hard-hitting and, as expected, Wyatt was committed to his character work throughout.
Indeed, the crowd was most engaged when the colorful nature of these characters was exploited to its full potential. When Undertaker responded to a Wyatt crab walk by sitting bolt upright, there was a bigger response in the arena than to any of the physical interactions between the two.
However, there was something missing from the bout that prevented it from being an above-average one. Despite kicking out of a Tombstone Piledriver, Wyatt simply wasn't positioned as being a real threat to Undertaker, which lowered the stakes.
15. Sycho Sid vs. Undertaker at WrestleMania 13
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Fighting on a canvas covered in bloodstains from Bret Hart vs. "Stone Cold" Steve Austin earlier in the night, Sid and Undertaker unfortunately couldn't match the best bout of the WrestleMania 13 card.
It was easy to see why this pairing was selected as a WrestleMania main event, as both men were leviathans who certainly fit the blueprint of top-tier talent under Vince McMahon's rule. However, size isn't everything, and Sid's lack of finesse sometimes caused the action to feel clunky.
However, at other times he was pristine. Seeing him pull off a textbook counter to the Tombstone Piledriver was really rather amazing, even if it wasn't quite enough to distract from his other weaknesses.
This certainly wasn't a bad match and would perhaps have stood out more at an earlier point on the show. However, as the main event, it's difficult to say that it was worthy of closing out the biggest card of the year.
14. Jake Roberts vs. Undertaker at WrestleMania VIII
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Still very early in Undertaker's career, the basic idea of this bout was whether or not Jake Roberts could weather the storm and survive his clash with Undertaker.
The Phenom wasn't as quick or as proficient as he would grow to be later on, but he was certainly elevated by a strong opponent and a clear sense of purpose to the match.
This was a minor WrestleMania match, clocking in at under 10 minutes and positioned early on the card. However, served its role in proceedings very well, offering up some memorable moments—Undertaker sitting up out of the DDT being particularly impactful—and definitely succeeded in continuing to build the legend of The Deadman.
13. Brock Lesnar vs. Undertaker at WrestleMania 30
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Brock Lesnar's death blow to The Streak was undoubtedly a WrestleMania moment that will go down in history, but the match itself wasn't an all-time classic.
Things were awkward from the start, partly due to the cautious actions of both competitors in the ring and the eerie hush cast over the arena throughout.
There were some highlights, of course. The action was consistently vicious on both sides of the equation. Lesnar got as good as he gave out—and there's no one who takes an Undertaker chokeslam quite as energetically as The Beast Incarnate.
The match was undeniably flat compared to the very best of Undertaker's WrestleMania standouts, but it was dramatic. The enormous impact of the result elevated the whole encounter, despite it not being the best effort of either man in terms of ring work.
12. Diesel vs. Undertaker at WrestleMania XII
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This underrated showdown between two of the biggest stars of the 1990s started out very strong, with a game Diesel providing the most competition to The Deadman at this point.
There was more variety than you might expect from the personnel involved at this stage in their careers, as both attempted to make this bout stand out as being worthy of The Showcase of the Immortals.
However, the bout lost some of its punch when it eased into a sedate middle section.
Things picked up with some entertaining action later on—the clash of two big boots and a ferocious Jackknife powerbomb from Diesel being two fun highlights.
Overall, it was a satisfying bout—a mid-table effort for Undertaker, but certainly among Diesel's better matches for the promotion.
11. Kane vs. Undertaker at WrestleMania XIV
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The better of the two WrestleMania encounters between The Brothers of Destruction, this match lived up to the larger-than-life nature of the storyline that linked Undertaker and Kane.
It was a wild brawl for the most part and made both men look every bit like unhinged supernatural forces. Kane was noticeable more agile and mobile than the likes of Diesel and Sycho Sid, which gives this match the edge over Undertaker's outings against those opponents.
The Phenom's leap onto Kane's shoulders—whatever tactical advantage he was hoping to gain from that manoeuvre—was a legitimately surprising display of athleticism. Moments later, his outside dive through a table was even more impressive.
It took three Tombstone Piledrivers to put away Kane in the end, which may sound like overkill but was appropriate given the intensity packed into this continually exciting bout.
10. Ric Flair vs. Undertaker at WrestleMania X8
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The best all-out brawl that Undertaker fought at WrestleMania, this 2002 clash with The Nature Boy was a bloody throwback to the No Holds Barred matches of years gone by.
Undertaker was perhaps at the peak of his powers as a villain here, hated by the crowd and clearly relishing the fact. His assault on Ric Flair was punctuated by casual pin attempts—most of which ended with The Deadman himself breaking the count.
Flair's first WrestleMania appearance in more than a decade featured plenty of claret, of course. Even Arn Anderson, interfering on his fellow Horseman's behalf, ended up donning the crimson mask before all was said and done.
There was no great plot to follow other than Big Evil taking liberties with a bona fide legend, but was still gripping stuff throughout. As a violent grudge match, this one definitely hit its mark.
9. Triple H vs. Undertaker at WrestleMania X-Seven
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The first of Undertaker's WrestleMania clashes with Triple H suffered from a preoccupation with brawling on the outside of the ring.
A lengthy scrap that didn't really add much to the bout set up a chokeslam and subsequent elbow drop from some scaffolding. While the live crowd loved the spot, the television broadcast seemingly did not do it justice.
The match improved significantly once the action returned to the ring and found its focus. Triple H's signature sledgehammer was implemented perfectly and played into a novel counter of the Last Ride.
An excellent closing stretch made you wonder how good this match could have been if so much time wasn't wasted in the early going. Still, it was so good in those closing moments that it's still an engaging encounter now.
8. Batista vs. Undertaker at WrestleMania 23
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An action-packed opening set the tone for this engaging fight from 2007.
Defending champion Batista was not well-liked by the Detroit crowd, but he no doubt won over some portion thanks to his impassioned performance.
What this bout lacked in finesse it certainly made up for in violence. Look to Undertaker's apron leg drop for an example of simple moves being imbued with some real venom—and if that's not enough evidence, check out the nasty powerslam through the announce table by Batista.
Both men put one another through the ringer, and by the end this one felt like a battle.
Eschewing the typical closing sequence of finisher attempts and reversals—likely because it wouldn't really play to Batista's strengths—a hot streak for The Animal was cut short by a somewhat out-of-nowhere Tombstone Piledriver.
It was a little bit anticlimactic but certainly worked for the live crowd. While this bout took a different path compared to the very best of Undertaker's WrestleMania output, it was a very engaging contest in its own right.
7. Randy Orton vs. Undertaker at WrestleMania 21
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It was difficult to think of a more ideal competitor to take on The Streak than Randy Orton in his Legend Killer persona.
The brash Orton started out strong, attempting to throw Undertaker off his game by cutting through his mystique. However, once Undertaker was able to strike back, his hits landed hard.
Orton was among the best of Undertaker's WrestleMania opponents in terms of making his offence look earth-shattering. Something as fundamentally basic as Old School looked positively destructive when delivered to the third-generation wrestler.
Indeed, technique was where this bout set itself from the pack. Both men were obviously incredibly proficient between the ropes, which allowed for some great sequences. The DDT counter to a Dragon Sleeper was the sort of thing that the likes of Batista and Diesel—while still having great matches with The Deadman—simply couldn't achieve.
Interference from Orton's father really seemed to convince the crowd that The Streak was in peril, and the arena lapped up everything that followed. In many ways, this was the bout that set the standard for The Streak's defense, as it was here where Undertaker's WrestleMania matches took on their extra significance.
6. CM Punk vs. Undertaker at WrestleMania 29
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The passing of Paul Bearer in 2013 made for the basis of a very personal feud between Undertaker and CM Punk at WrestleMania 29.
Whether or not you were happy with the way WWE used real-life tragedy to fuel a WrestleMania storyline, it's difficult to deny that the match between Punk and The Phenom was one of the best Undertaker has had at the event.
The Straight Edge Superstar attempted to break The Streak with a slightly different strategy to most of his predecessors. He was eager to throw The Deadman off his game, and his cocky attitude was the perfect foil for Undertaker's seething rage at the disrespect he was being shown.
The result was a very physical encounter, with spots like Punk's brutal elbow drop to the announce table really hitting hard.
There were the typical false finishes and near-falls, but they were all implemented to their maximum potential. The sequence that led to Punk kicking out of the Tombstone Piledriver made the moment much more impactful than other occasions where the manoeuvre failed to pick up the win.
While the technique on display never quite reached the heights of Undertaker vs. Shawn Michaels, the energy levels from competitors and crowd did come close. As CM Punk's final WrestleMania performance, it was a real high point at which to go out.
5. Triple H vs. Undertaker at WrestleMania XXVIII
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By far the better of Undertaker's two Hell in a Cell matches at WrestleMania to date, this bout from 2012 may not have been the "end of an era" but was certainly something of an epic.
The Hell in a Cell stipulation might have seemed to be the biggest difference between this match and the one from the year before, but it was special referee Shawn Michaels who put the most distance between the two. He was vital to the drama of proceedings and played his role perfectly.
The gist was that HBK could easily bring The Streak to an end as an official, whereas he couldn't as an active competitor. However, when he was given the opportunity to end the match due to a Triple H beatdown, he relented and let Undertaker take his fate into his own hands. It was a relatively simple storyline that was delivered perfectly over the course of the match.
Unfortunately, the encounter wasn't without its faults. It was a long slog, as it needed to be, but that resulted in some slow sections around the midpoint. It's not quite so noticeable watching the match by itself, but in the middle of a four-hour card, it was a little exhausting.
However, a strong finish closed things out the right way. There were some rough edges here, but the match still ranks among the best work these three legends ever delivered at The Showcase of the Immortals.
4. Triple H vs. Undertaker at WrestleMania XXVII
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The second of Triple H and Undertaker's trilogy of WrestleMania matches was the best of the three, in large part because it played to both men's strengths in the ring.
While their clash at X-7 spent too much time brawling through the crowd and their Hell in a Cell encounter played more on interpersonal drama, here the wrestling was the central component. As a result, it was a very satisfying match.
Triple H's assault on The Streak was the focus, as The Game threw everything he could at The Deadman in an attempt to avenge his best friend, Shawn Michaels.
Filled with finishers and near-falls, there was an undeniable scale to this match. The competitors involved would of course have made this an epic no matter what, but the content of the bout really drove home the fact that both would put themselves—and their opponent—through hell to get the win.
If there's a criticism to be made of the match, it's that it seemed like a follow-up to HBK's encounters with The Deadman that never really reached the heights of WrestleManias 25 and 26. That said, it was still an excellent example of the WWE main event style playing out at its biggest showcase.
3. Shawn Michaels vs. Undertaker at WrestleMania XXVI
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The second WrestleMania match between Undertaker and Shawn Michaels couldn't quite live up to the impossibly high standard set by its predecessor, but it was certainly a game attempt.
With the stakes raised thanks to its career-ending stipulation for HBK, it's clear from the bell that the competitors had no interest in simply retracing their steps. A pacier opening sequence set the tone for a fight that was sufficiently distinct from their earlier meeting.
Michaels' behaviour in trying to get the match during the build and his sheer influence before the bout got underway demonstrated a clever tweak to his character. He was certainly much more aggressive than he was at WrestleMania 25, eager to claim the win rather than eke out a victory.
Both men had diverse war crates at their disposal, but even their signature moves were used with great creativity in this standout return match. HBK demonstrated every inch of his abilities in his final bout, from his technical strength in a pinfall counter to Hell's Gate to the spectacle of his remarkable moonsault onto the announce table.
Of course, by the end, the match concentrated on interpersonal drama rather than wrestling acumen. "No one wants The Streak to end, no one wants the career to end," Michael Cole observed on commentary. "Something has to give at WrestleMania."
Undertaker's breaking from a taunt to simply tell HBK to stay down was a classic moment of wrestling pathos. Michaels remained defiant to the last, provoking a memorable end to the match—and to his legendary career.
2. Edge vs. Undertaker at WrestleMania XXIV
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While the feud between Edge and Undertaker might not have the epic status of the clashes The Phenom had with the likes of Shawn Michaels and Triple H, this was certainly a standout WrestleMania match.
A big reason that this bout stood out from the crowd so well is the way it subverted expectations of Undertaker defending his streak. Edge's strategy from the outset was to look past the mind games and concentrate on working the back—very appropriate for the era and for his character.
Of course, by the end of the bout, Edge found out that Undertaker's mind games were more than just a tactic. Beyond being a great match in its own right, this encounter did a great deal to orient The Deadman persona in the more grounded WWE landscape of the 2000s.
Aside from the thematic strength of the match, the physical action really shined. The WrestleMania main event came as part of a lengthy feud between the two—neatly referenced via the use of a camera as a foreign object, calling back to Edge's subterfuge at Survivor Series 2007.
As well as raising the stakes for this bout, that familiarity was evidenced by the chemistry Edge and Undertaker shared between the ropes. Effortless counters like the neat reversal of a chokeslam attempt into a DDT helped elevate this encounter above some of The Deadman's very best WrestleMania performances.
This lengthy match started off slow, gradually ratcheting up the pace throughout. There was something pleasingly old-school about the feel of the bout as a result, and it was very appropriate as the show closer.
An attempt at interference from Curt Hawkins and Zack Ryder led to a near-fall off a spear that brought the crowd to its feet. The finish—a second spear reversed into Hell's Gate—was a fitting end to a true WrestleMania epic.
1. Shawn Michaels vs. Undertaker at WrestleMania 25
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The epic clash between Undertaker and Shawn Michaels from the 25th anniversary of WrestleMania is quite rightly considered one of the best to ever appear on the show.
It was a summation of everything that The Showcase of the Immortals promises to offer—the biggest stars in the industry giving their best on the grandest stage, with a hot crowd invested in every exchange.
The early going set up the two important contrasts between The Phenom and The Showstopper. There was the physical difference, in that Undertaker's power was counteracted by Michaels' quickness and agility, and there was the defiance that HBK threw in the face of The Deadman's dominance.
Everything from the competitors' ring entrances onwards served to reinforce the distance between the two competitors. It really inflated the momentous nature of the bout beyond a simple grudge match.
The turning point of this bout came when an outside dive attempt by Undertaker was thwarted by Michaels, who employed a nearby cameraman to take the brunt of the impact. The Deadman was almost counted out as a result, smartly playing on the crowd's loyalties.
From this point onwards, the competitors had the live audience exactly where they wanted them, and every single exchange got an enormous response.
Undertaker hit a thunderous chokeslam. Michaels skinned the cat—only to be caught in a Tombstone Piledriver—which he somehow managed to kick out from. The action simply didn't stop, which was all the evidence you would ever need that these two wrestlers were masters of their craft. A really amazing finish capped off a supreme closing stretch.
There's often a great deal of discussion at this time of year about what makes a match worthy of WrestleMania, and while there are many aspects to consider, you could certainly answer the question by working backwards from this legendary encounter.
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