Ranking Every WWE WrestleMania Match of The Undertaker's Legendary Career
Those first few matches against the legendary likes of Jimmy Snuka and Jake "The Snake" Roberts were far from barnburners, but they successfully laid the groundwork for what was to come in the years that followed. In fact, his outings on The Grandest Stage of Them All only improved.
Superstars such as Shawn Michaels, Triple H, Batista and Edge all brought the best out The Phenom when the lights were on bright and produced some of the strongest matches to ever take place at the event. Memories were made, moments were created, and the legacies were solidified during this period.
Of course, all good things must come to an end, and in 2014, 'Taker suffered a shocking defeat at WrestleMania 30 at the hands of Brock Lesnar. A decent contingent of fans thought that was it for him, until he returned to the ring the following year at 'Mania and has competed at almost every installment since.
At WrestleMania 36, he wrestled what will very likely end up being his final match and went out on top against AJ Styles. From a Boneyard bout to three Hell in a Cell clashes to everything else in between, The Deadman has done it all at The Show of Shows and will be forever remembered as a WrestleMania legend.
Now that his career has come to a close, let's look back at every 'Mania match Undertaker has had dating back to his debut at the spring spectacle in 1991. Criteria for ranking them from worst to best will include historical significance, overall action, build, storytelling and crowd engagement.
27. vs. Giant Gonzalez (WrestleMania 9)
For as many awful matches as Undertaker has had at WrestleMania over the years—and there's been a handful of duds as you'll soon see on this list—none of them quite reached the lows that this one did.
Following two straightforward squashes at WrestleMania, Undertaker met his first real challenge in Giant Gonzalez, who had debuted at the 1993 Royal Rumble event and eliminated The Deadman. It was meant to be a clash of titans but wound up being a complete disaster.
Although Undertaker wasn't having instant classics at this stage of his career, he was at least capable of having a competent match, provided he had the proper opponent. Unfortunately, Gonzalez was not that person, and as a result, their encounter was about as atrocious as you can imagine.
WrestleMania 9 was far from a great 'Mania anyway, but this bout arguably brought it down an entire letter grade. Despite his large size, Gonzalez didn't look intimidating in the slightest thanks to his goofy body suit, not to mention that his his in-ring skills (of lack thereof) shouldn't have put him in contention for a match at WWE's biggest show of the year.
The disqualification ending, which led to the feud's continuation through SummerSlam, undoubtedly makes this one of the worst WrestleMania matches of all time, let alone Undertaker's.
26. vs. Big Bossman (WrestleMania 15)
Not only this at the bottom of the barrel of Undertaker's WrestleMania performances, it also lays claim to being the worst Hell in a Cell match in WWE history.
For as great of a character as Bossman was, he was an odd opponent for Undertaker at WrestleMania 15. He was very much in the thick of things on WWE TV at the time, but this felt like an undercard affair with an unnecessary stipulation tacked onto it.
There was virtually no story behind the bout and almost no action, either. Rather, they brawled for the entire time before Undertaker mercifully put Bossman away for the victory.
His attempt to hang Bossman from the top of the structure afterward was in bad taste and ended this train wreck on the worst note possible. The bout was bad enough for WWE to omit it from its Hell in a Cell DVD compilation released in October 2008, which featured every installment of the match up to that point except for that one.
This is one of the more forgettable 'Mania matches Undertaker has ever had and rightfully so.
25. vs. King Kong Bundy (WrestleMania 11)
WrestleMania 11 is right up there with WrestleMania 9 as an all-time terrible WrestleMania. Once again, Undertaker's match that evening was a significant reason for that.
The entire year of 1995 was a career lowlight for The Phenom. Coming off a stretch of subpar matches the previous year, 1995 was no different thanks to seemingly never-ending rivalry with Ted DiBiase's Million Dollar Corporation.
Fans had already suffered enough after Undertaker demolished I.R.S. at the Royal Rumble, yet WWE decided to make matters even worse by putting King Kong Bundy up against 'Taker at WrestleMania 11. Bundy had his role in WWE history and deserves to be in the WWE Hall of Fame for the impact he had on the industry, but by 1995, his matches were almost unbearable to sit through.
Undertaker's urn at ringside was the clear focal point, but everything else about this was dreadfully boring. Even at six minutes in length, it was longer than it needed to be and the outcome was never in doubt.
You're bound to find more excitement in a three-hour Raw than you would from re-watching this painfully slow dreck.
24. vs. Jimmy Snuka (WrestleMania 7)
Interestingly enough, the match where The Streak got started wasn't much of a match at all.
Undertaker was still relatively new on the WWE scene by early 1991. He had just arrived at Survivor Series months earlier and was running through every opponent put in front of him.
Despite there being no stakes or consequences to his WrestleMania 7 clash with Jimmy Snuka, it was a big deal nonetheless considering everything Superfly had accomplished in his career up to that point. He wasn't doing anything of note at the time, and 'Taker was the perfect person for him to help elevate by losing to him.
There was nothing that could have made the bout better, so booking like a showcase for Undertaker was the correct call. He decimated the WWE Hall of Famer with ease and pinned him with an emphatic Tombstone for the three-count.
This outing is obviously historically significant because of what would come out of it, but the match itself is pretty paint-by-number stuff. If you are willing to re-watch it, then at least you won't be wasting more than four minutes of your time.
23. vs. Big Show and A-Train (WrestleMania 19)
There's no telling how much better—or worse—this WrestleMania match would have been with Nathan Jones involved as originally planned.
The Australian up-and-comer was in the midst of an aggressive push at the time and was pegged to partner with Undertaker at WrestleMania 19 against the duo of Big Show and A-Train. It would have been the first and only time 'Taker teamed with anyone on the grand stage, but either way, it was going to be a massive waste of his talent and star power.
It was entirely designed to benefit Jones and cement him as a star, but whether that would have worked or not is unknown. Before the bout could take place, Jones was attacked backstage, leaving 'Taker to fend for himself against two equally large athletes.
Despite having the odds stacked against him, Undertaker still managed to emerge victorious. This was around the time that fans started to take notice of The Streak, so there was no way he was going to lose and the match was as plodding as could be.
As for Jones, unsurprisingly, his WWE career didn't pan out and he was gone less than a year later.
22. vs. Jake Roberts (WrestleMania 8)
By 1992, Undertaker was basically a full-fledged babyface. Crowds had been cheering him on for a while by that point, but he needed a vile villain to work against so he could solidify his status as a fan favorite.
Enter Jake "The Snake" Roberts.
Undertaker and Roberts were aligned for many months as 'Taker assisted Roberts throughout his feud with Randy Savage. Savage vs. Roberts should have been the match at 'Mania, but WWE went in a different direction by putting Savage back in the WWE Championship picture instead.
That left Roberts without a dance partner at WrestleMania 8, and Undertaker made as much sense as anyone. Roberts was at the end of his run as an active performer at that point, so while a great match was going to be hard to come by, it effectively got The Deadman over as dominant.
Their six-minute affair was fine for what it was and achieved what it needed to, but it isn't anything you need to seek out compared to classics coming later on in this list.
21. vs. John Cena (WrestleMania 34)
How does one accurately rank a match that featured two of the biggest names in wrestling history facing off and lasted all of two minutes?
The build to Undertaker vs. John Cena at WrestleMania 34 was incredibly bizarre, to say the least. The Deadman seemingly wrestled his final match the year prior against Roman Reigns at WrestleMania 33, but as he explained on The Last Ride documentary in 2020, he hated his performance so much that he decided he couldn't call it a career on such a sour note.
That led him to a match at 'Mania in 2018, except it wasn't made official until the weekend of the event. WWE spent months teasing Cena vs. Undertaker for WrestleMania 34, but there was no actual advertisement of it in the weeks preceding the pay-per-view.
Undertaker later explained that he trained extensively to get ready for his anticipated return to the ring. He looked to be in spectacular shape when he walked down the ramp to answer Cena's challenge for an impromptu 'Mania match, giving fans hope it would be the epic encounter they had long waited for.
What we got instead was a one-sided two-minute squash: Undertaker hit all of his signature moves, no-sold Cena's offense and put him away in decisive fashion. As a moment, it was memorable, but as a match, it was disappointing for those expecting more.
20. Vs. Sycho Sid (WrestleMania 13)
Undertaker's premiere WrestleMania main event was unfortunately a letdown.
Other than a two-day run as WWE champion in late 1991, he didn't hold any world titles for the first stretch of his WWE career. He finally entered the title picture in early 1997, but the champion at the time was none other than Sycho Sid.
That isn't to say Sid was a mediocre performer by any means, especially since he and Shawn Michaels contested a classic at Survivor Series a few months earlier. Unlike The Heartbreak Kid, however, Sid lacked chemistry with 'Taker, and the two had a fairly dull 'Mania main event.
There have been significantly worse main events in WrestleMania history, but this would rank closer to the bottom of the list than it would near the top. After an already lousy event, they had the tough task of closing out the evening with an exhilarating affair and failed miserably.
It was going to be impossible for them to top Bret Hart vs. "Stone Cold" Steve Austin, but at the very least, they could have had an entertaining match in that main event slot. It was way longer than it needed to be, and Undertaker's title win was the sole saving grace.
19. vs. Roman Reigns (WrestleMania 33)
Three of Undertaker's best WrestleMania matches came in the main event position, while the other two were among his worst. As previously mentioned, his match with Sycho Sid was a mess, and his outing against Roman Reigns at WrestleMania 33 was only marginally better.
The story itself of Reigns trying to rid WWE of Undertaker and steal "his yard" was actually somewhat compelling. Seeing 'Taker mix it up with the younger guys in recent years has been refreshing, and Reigns looked like the perfect opponent for him on paper.
The bell ringing was the beginning of the end for this encounter. Undertaker looked awful physically and had no business being in the ring that year. Not even Reigns could make this match worthwhile.
The attempt was there, but Reigns clearly had to carry 'Taker through the entire match. The only redeeming aspect of it was the emphasis on storytelling, with Undertaker refusing to stay down and powering out of everything Reigns was dishing out.
It was rough to sit through and especially sad knowing that it was supposed to be Undertaker's final farewell. Reigns did his best to salvage any credibility 'Taker had left, but it was painfully apparent The Phenom was far from what he once was and that a win over him would mean a lot less than it would have years earlier.
18. vs. Kane (WrestleMania 20)
Undertaker vs. Kane is one of the greatest stories WWE has ever told, but their feud will be remembered more for their promos and segments than their interactions inside the ring.
The on-screen brothers first met one-on-one at WrestleMania 15 and continued to clash on occasion in the years that followed. When they rekindled their rivalry at Survivor Series 2003, it was under completely different circumstances.
At the time, Undertaker was portraying his American Badass persona, while Kane had just unmasked for the first time in his WWE career. Kane buried his brother alive, which paved the way for 'Taker to return with the classic Deadman gimmick at WrestleMania 20.
The buildup to the bout was very well done, and the sight of Undertaker making his iconic entrance at Madison Square Garden with Paul Bearer by his side was surreal. That moment alone earns this match a spot in the top 20, even though the actual wrestling was below average.
It was essentially a "best of" for The Phenom than it was a true competitive contest. Kane wasn't nearly as much of a threat coming out of it the same way he was in 1998 following their first encounter, but the crowd was satisfied with what they saw and that was all that mattered.
17. vs. Mark Henry (WrestleMania 22)
Before the Hall of Pain came to be, Mark Henry had has first major run as a top heel on SmackDown in 2006. He was unsuccessful in becoming the world heavyweight champion on a few occasions and then set his sights on Undertaker's undefeated streak at WrestleMania 22.
For as much momentum as Henry had at the time, his matches were still substandard for a main event player. As for Undertaker, he was coming off an excellent encounter with Randy Orton the year prior, so the bar was set pretty high heading into their outing on The Grandest Stage of Them All.
To make matters more interesting, WWE added a Casket stipulation to the bout. That meant Undertaker didn't have to get pinned in order to lose, so there was a bit more drama surrounding the outcome than there usually was.
It was a fine concept, but the two failed to produce a WrestleMania-worthy match. It wasn't remotely as bad as some of the other aforementioned matches, but it didn't generate much excitement and solely existed to extend The Streak another year.
The effort was there, but the execution was less than stellar.
16. vs. Brock Lesnar (WrestleMania 30)
Anyone who has followed the careers of Undertaker and Brock Lesnar is well aware that they are no strangers to one another.
Lesnar's feud with Undertaker in 2002 helped put him on the map and made him more of a main event star than he already was. In addition to rekindling their rivalry in 2003, they also quickly crossed paths at a UFC event in October 2010 following Lesnar's loss to Cain Velasquez and had a heated exchange.
All of that history got fans excited for their next collision at WrestleMania 30. Undertaker had never before beaten The Beast by pinfall or submission, and now he'd have to do it on a stage he had never lost.
The story essentially wrote itself, but contest was a catastrophe, largely because Undertaker was concussed within minutes of the match starting. They hit all of their biggest moves and had the crowd engaged for a majority of it, but it wasn't the hard-hitting affair they were hoping for because of Undertaker's injury.
That resulted in the bout feeling like it dragged on forever until Undertaker was finally pinned for a three-count by Lesnar, much to the shock and dismay of the audience in attendance and everyone else watching around the world. It's arguably the most shocking moment in WWE history, and yet the match was a massive disappointment.
Thankfully, they went on to have better matches against each other in 2015, but it's safe to say 'Taker lost a little bit of himself in the ring that night he never got back.
15. vs. Shane McMahon (WrestleMania 32)
At least Undertaker had his concussion to blame for his bout with Brock Lesnar being as boring as it was. His WrestleMania 32 match with Shane McMahon was boring simply because those two had no business facing each other at that stage of their careers.
Present day, Undertaker vs. Shane McMahon doesn't sound like an appealing match on paper, but at the time, fans were willing to excuse the lack of logic because Shane had just made his shocking return to WWE after almost seven years away. He wanted complete control of the company, but in order to get it, he had to go through Vince McMahon's hand-picked opponent for him: The Undertaker.
Bizarrely enough, Undertaker was an afterthought throughout the build to 'Mania. He hardly showed up on WWE TV, and the focus was almost entirely on the McMahon family drama. That would mostly explain why the match was a mess, in addition to both men being past their physical primes.
The Hell in a Cell stipulation was only added to make it more of a spectacle, and to a degree, it worked. Shane's leap off the top of the structure on top of 'Taker will never be forgotten, but the rest of the matchup absolutely will be.
It was comical to think that Undertaker would have trouble defeating a non-wrestler who hadn't competed in nearly a decade, causing the match to drag beyond belief. When Undertaker finally put him away with a Tombstone, he couldn't have done it fast enough.
The worst part was that Shane took the reins of Raw the very next night despite losing to Undertaker, rendering their match completely pointless. We also never found out what was in that lockbox of Vince's, but that's another story for another day.
14. vs. Bray Wyatt (WrestleMania 31)
Coming off Undertaker's vastly disappointing WrestleMania match with Brock Lesnar, it was almost impossible for his WrestleMania outing against Bray Wyatt to be any worse, especially if he managed to stay healthy and not get immediately concussed.
Compared to his clash with Lesnar, his WrestleMania match with Bray Wyatt in 2015 was a vast improvement. Compared to the 'Mania matches he had when The Streak was still intact, it felt like it belonged on an episode of Raw or SmackDown.
To Wyatt's credit, he had been so creatively damaged by 2015 that no one actually thought he would defeat The Deadman. The Streak was no longer in play and that hurt fans' interest in the match, though there was the curiosity factor of wondering what he would look like after a year away.
Sure enough, Undertaker emerged with his hair grown out for the first time since 2011 and was moving around a lot better. Wyatt vs. Undertaker was a cool clash of characters and served as a fine way to reintroduce The Phenom, but this was never going to be a five-star mat classic.
It also did nothing to benefit Wyatt, who disappeared for months until kicking off his rivalry with Roman Reigns.
13. vs. Kane (WrestleMania 15)
As previously noted, you aren't bound to find any of the the matches Undertaker and Kane had on a list of the best ever in WWE history, but the stories they told together were nothing short of magical with the first trumping the rest that came after it.
Kane's well-documented debut at Badd Blood 1997 led to him playing mind games with Undertaker in the remainder of the year. It wasn't until he burned his brother alive at the Royal Rumble that 'Taker finally agreed to face his flesh and blood at WrestleMania 15.
Undertaker defeated almost every opponent he had at WrestleMania up to that point with ease. Kane was much more of a threat than anyone he had ever faced before, which was evident when he kicked out of two Tombstones from 'Taker.
Fans truly believed that Undertaker would meet his demise at the hands of Kane. He was booked that well and came across like an equal to Undertaker, so much so that he maintained that momentum following the pay-per-view and became a household name that is now preparing to enter the WWE Hall of Fame as part of the 2021 class.
At WrestleMania 15, it was a horror movie come to life as Undertaker gave Kane one of his most memorable matches of his career.
12. vs. Diesel (WrestleMania 12)
Diesel catches a lot of flack for fans for his yearlong WWE Championship reign coming at one of the worst periods financially for WWE, not to mention that most of his matches were substandard. That said, his best bouts in the company were against Bret Hart, Shawn Michaels and Undertaker.
It isn't difficult to see why he'd have quality chemistry with either Hart or Michaels, who are widely regarded as two of the greatest wrestlers to ever lace up a pair of boots. Undertaker, on the other hand, typically had terrible matches with men who were around his size, so this shouldn't have been much different.
However, it ended up exceeding expectations and being an enjoyable affair. There were a few points where the action slowed down and wasn't very riveting, but otherwise, this was an excellent big-man bout, even by today's standards.
It was pretty apparent by early 1996 that Diesel was on his way out of the company, so it was a pleasant surprise that WWE put him in a prominent position in his final 'Mania match against a notable namex. Better yet, it wasn't a one-sided squash, and Diesel was allowed to have one of his most impressive performances ever.
Every WrestleMania match Undertaker had in the 1990s was a bust except for this one.
11. vs. Ric Flair (WrestleMania 18)
The Ric Flair who came to WWE in 2001 had way more mileage than the Ric Flair who initially signed with WWE in 1991. His first run with the company was short, sweet and successful, whereas the next decade he spent in WCW was filled with head-scratching moments and horrible matches.
Flair has said in many interviews that he never intended on wrestling when he returned to WWE upon the closure of WCW. He resurfaced as an authority figure, but his Street Fight with Mr. McMahon at the 2002 Royal Rumble restored some of his confidence that he could be The Nature Boy of old.
Undertaker has also discussed on Broken Skull Sessions with Steve Austin that he had fallen through the cracks creatively leading up to WrestleMania 18 and that WWE didn't have an opponent in mind for him. Vince presented him with the choice of facing either Flair or Rob Van Dam, and he chose the former WWE champion without hesitation.
It had every reason to be bad but wasn't. Flair put in a commendable performance and that pushed 'Taker to be the best he had been at WrestleMania up to that point. Even the interference from Arn Anderson, Flair's Four Horsemen stablemate, was well received by the audience and added an extra layer to the bout.
All in all, it was a really good match that resulted in Flair becoming an active member of the roster for another six years. This was also where The Streak was acknowledged for the first time and spawned many amazing matches that you'll find in the top 10 of this list.
10. vs. Randy Orton (WrestleMania 21)
Despite his time spent in Evolution and winning the World Heavyweight Championship at the age of 24, Randy Orton was still an unproven commodity as a singles star in 2005. His face run flopped and it would have been easy for him to slide down the card, never to experience main event stardom again.
Instead of settling for second-best, Orton bounced back in a big way by reverting to his roots as a heel and going after Undertaker ahead of WrestleMania 21. He wanted to be the one to end Taker's undefeated streak at The Show of Shows, and truth be told, he came closer than almost anyone.
If anyone was going to benefit from defeating The Deadman and getting that big boost, it was Orton. He had so much potential but was lacking a standout performance on a stage such as 'Mania. This was it.
They went on to have better bouts together in the remainder of 2005, but this was still an entertaining encounter that is mostly remembered for the strong showing Orton had. That RKO out of nowhere was the signature spot of the match and nearly earned Orton the victory, but all it took was a Tombstone for Undertaker to silence The Legend Killer.
This was a prime example of how a young up-and-comer can gain a ton, even in defeat.
9. vs. AJ Styles (WrestleMania 36: Night 1)
Undertaker vs. AJ Styles would have no doubt been higher on this list had it taken place a decade sooner, but it was better than late than never, considering the spectacle it ended up being.
The circumstances surrounding WrestleMania 36 put everyone in a tough position, with some matches having to be changed or outright canceled. Undertaker and Styles were always on track to have a standard singles affair at WrestleMania, but the pandemic forced them to get creative so that they didn't have to wrestle in an empty building.
Needless to say, this match would have looked a lot different inside the Performance Center and wouldn't have been remotely the same. They were able to make the most of a bad situation by taking a cinematic approach and shooting the entire thing in a gloomy boneyard in the middle of nowhere.
The added effects and background music made it a masterpiece that worked around Undertaker's limitations. He also had the chance to return to his American Badass person for one night only, and it was extremely fitting given the environment they were in.
It wasn't the wrestling classic Styles and even Undertaker have been known to have in their careers, but it was still a blast and the perfect way to close out Night 1 of WrestleMania 36. Above all else, it helped fans forget about the pandemic if only for a brief bit and allowed them to enjoy something unprecedented.
8. vs. Triple H (WrestleMania 17)
As two stalwarts of WWE's Attitude Era, Undertaker and Triple H have a very rich history together. Their long list of battles over the years from vastly underwhelming to incredibly great. Thankfully, their WrestleMania 17 match fell in the latter category.
Triple H was coming off one of his best in-ring years ever in 2000. He held the WWE Championship on multiple occasions and owned victories over the likes of "Stone Cold" Steve Austin, The Rock, Kurt Angle and Mick Foley.
Although The Streak wasn't an attraction yet, he had a tough task in front of him when he challenged Undertaker to a match at 'Mania in 2001. Of course, WrestleMania 17 is considered to be the best of all time (and for good reason), and among a stacked card, these two managed to stand out with a stellar outing.
They brawled all around the arena and fed off the electric atmosphere. The Deadman took his time decimating Triple H, while The Game took every shortcut he could in attempt to steal the victory.
The only knock against this match is that it didn't have a No Disqualification stipulation, which you think it would watching it. The referee refusing to call for the bell at several points was slightly strange, but that's merely picking as the rest of this bout was a real treat.
7. vs. Batista (WrestleMania 23)
For almost a decade-and-a-half, Undertaker lacked that one standout WrestleMania match. His battles with Diesel and Kane were the best of the bunch, but neither of them stole the show they occurred at.
It had been a decade since Undertaker compete for a world title at WrestleMania, but in 2007, he earned the right to do so when he won the Royal Rumble. He chose Batista as his opponent soon after, someone he had never crossed paths with one-on-one.
Batista had been on the rise for two years and seemed to be the unbeatable world heavyweight champion. Unlike Undertaker's past opponents, Batista showed no fear in the face of The Phenom and took the fight to him the moment the bell rang at WrestleMania 23.
WWE's odd decision to put them on in the middle of the show and not in the main event actually fueled them to have a match that would be talked about for years to come—and it was. They went all-out, kept the crowd engaged throughout and had a barnburner of a bout.
Batista would have been a fine choice to end The Streak, but it was perfectly acceptable that he didn't. In fact, he went on to beat Undertaker in two more matches later that year, so Undertaker did a lot to further establish Batista as a top star in the industry.
6. vs. CM Punk (WrestleMania 29)
For all intents and purposes, CM Punk deserved to be in the main event of WrestleMania 29. He reigned as WWE champion for the latter half of 2011 and all of 2012, yet John Cena vs. The Rock took precedence and forced Punk to find another opponent on the undercard.
Undertaker was without a dance partner as well, and with the roll Punk was on as a heel at that point, he was a fantastic foil for him. WWE quickly had to come up with a reason for why they would face each other and settled on Punk winning a Fatal 4-Way and earning the right to challenge The Streak at WrestleMania 29.
It wasn't a creative approach, but Paul Bearer's abrupt and unfortunate death led to the company incorporating that into the storyline. Punk acted disrespectful toward 'Taker and wanted nothing more to get his hands on him to avenge his fallen father figure.
The storytelling was solid, but the in-ring action was wonderful. It can be argued that Punk carried Undertaker to a terrific match, but The Deadman more than held his own in what would be his last great 'Mania match until facing AJ Styles in 2020.
As for Punk, if he never wrestles again, this was an awesome match to hang his hat on as being his last to take place at WrestleMania.
5. vs. Triple H (WrestleMania 27)
The Undertaker vs. Shawn Michaels WrestleMania matches left fans wondering what was next and who was going to step up to challenge 'Taker for his streak starting at WrestleMania 27. The only logical person who could do so was Triple H, someone near and dear to Michaels and had as good of a chance as anyone of snapping The Streak.
They had already waged war a decade earlier at WrestleMania 17, but The Game was much more seasoned this time around, and Undertaker was showing signs of ring rust as a part-timer. This was his opportunity to capitalize on Undertaker's weaknesses and do what no other man ever could.
Their first faceoff on Raw in February 2011, marking their first appearances on WWE TV in many months, gave goosebumps to everyone watching that night. With a single glare at the WrestleMania sign, they had viewers hooked.
They needed to go outside of the box for their bout to ensure they weren't following the same formula as Undertaker's matches with Michaels. The No Holds Barred stipulation helped with that and allowed them to brawl around ringside, battering each other with everything they could find.
Triple H put in an unbelievable effort and hit Undertaker with multiple Pedigrees and even a Tombstone. Undertaker powered out of them all and needed three Tombstones of his own to defeat The Game.
The suspense surrounding The Streak made this match much better than it would have been otherwise. Nonetheless, it was an outstanding affair and one of the few saving graces from what was an uneventful WrestleMania.
4. vs. Edge (WrestleMania 24)
After every attempt to stay at the main event level, including during his feud with John Cena in 2006, Edge would almost always fall back down the card. He held the top title on SmackDown for a portion of 2007, but an injury prevented him from becoming the face of SmackDown for more than a few months.
His climb to the top of the card started with a Money in the Bank cash-in on Undertaker, a story that played itself out over the next year. He cost 'Taker the World Heavyweight Championship at Survivor Series 2007 and won it the next month at Armageddon, putting Undertaker in prime position to chase him en route to WrestleMania 24.
The Phenom had to overcome every obstacle imaginable to even make it to 'Mania, where Edge promised victory because he too had never experienced singles defeat at The Show of Shows. With the world title up for grabs, their match had a big-fight feel and they did not disappoint.
Edge was the quintessential slimy heel in going to great lengths to ensure Undertaker wouldn't win. None of his shenanigans worked, and when 'Taker nailed him with a Tombstone, the crowd exploded in elation knowing they had a new champion.
WWE made the right choice in putting this on last at WrestleMania 24 as it was the best bout of the night and proved to be a masterclass in storytelling and exhilarating action.
3. vs. Triple H (WrestleMania 28)
Nothing was going to top Undertaker's back-to-back bouts with Shawn Michaels at WrestleMania, but this sure came close.
In January 2012, Triple H was approached by Undertaker, who desperately wanted a rematch after failing to leave the ring the year before on his own two feet. He won the battle the night of WrestleMania 27 but not the war, at least in his mind.
Triple H eventually agreed, and to make the deal even sweeter, Shawn Michaels was appointed the special guest referee with a Hell in a Cell stipulation to boot. There were a ton of moving parts, but all it made sense given their history inside the structure and Michaels' own history with both men.
This was another one of those Undertaker matches that should have been subpar because of how he and Triple H were approaching the end of in-ring careers, but with how strong the storytelling was, they made fans forget that fact. Instead, they took them on a journey where they were invested every step of the way.
Michaels' Sweet Chin Music to Undertaker following by Triple H's Pedigree made an amazing near-fall, one of the most suspenseful ever. WWE did a exceptional job of making fans believe this could really be it for The Streak, even though it wasn't.
The End of an Era tagline didn't ring true because all three men continued to compete in the years that followed (including against each other), but that final image of them standing at the top of the stage looking out into the crowd was remarkable.
2. vs. Shawn Michaels (WrestleMania 26)
A worthy rematch in wrestling is hard to come by. Even outside of the squared circle, it's well known that sequels are almost never on the same level as the original in a series or franchise.
Not only did fans clamor for another round of Undertaker vs. Shawn Michaels following their instant classic at WrestleMania 25, it lived up to the hype and spectacularly so.
They took a different approach this time around. Instead of Michaels acting cocky because he had the advantage over Undertaker (who had never defeated him one-on-one prior to 2009), he was distraught over the loss because he knew he could have won had things gone slightly different.
The next year saw him spiral out of control, from almost quitting the business entirely to be a short-order cook to losing the tag titles with Triple H to attacking a referee after losing in the Royal Rumble. Costing Undertaker the World Heavyweight Championship was the only way he could get his attention and force him to agree to a rematch.
Even the atmosphere in the building the night of their WrestleMania rematch was different because the stakes had changed; in addition to Undertaker's Streak being on the line, so was Michaels' career. He fought with every ounce of his being but still fell short in the end to a jumping Tombstone, no less.
The look of sheer sadness as well as the relief on the face of Michaels as he embraced Undertaker afterward and walked up the ramp to call it a career made for a beautiful image. You couldn't have asked for a better retirement match from a legend of his stature.
1. vs. Shawn Michaels (WrestleMania 25)
It's been discussed ad nauseum over the last decade-plus, and yet watching this masterpiece back year after year will never get old to anyone who claims to be a diehard wrestling fan.
Anything you can ask for out of a match, this had it. If you're looking for a match to show a non-fan and attempt to get them hooked on the product, this is it. It's the measuring stick when it comes to not only Undertaker matches but also the greatest matches in WrestleMania history—or just in general.
It's pure perfection.
Shawn Michaels and Undertaker had their fair share of wars before, specifically in 1997 and 1998, and it was evident then that their chemistry in the ring was second to none. Even on their worst day, they could have an excellent match, and that remained true over a decade later when they collided for the first time at WrestleMania.
The story was simple: Undertaker was never able to beat Michaels in his career, but he was also undefeated on The Grandest Stage of Them All, the same stage where The Heartbreak Kid had shown up and showed out time and time again.
The buildup was brilliant, the entrances were unforgettable, and the match itself was exceptional. This was back when near-falls were still fairly rare, so you could feel every kickout from both men. The electricity in the air that night was palpable.
A moonsault-turned-Tombstone earned Undertaker the hard-fought victory. No match on this list will ever stand the test of time the same way, for its flawlessness will forever keep it in a league all of its own.