Introduction – Best Undertaker Matches
So, let’s take a look at The Undertaker. Actually, how long do you have? Because his 30-year WWF/WWE career ranks alongside anybody’s in history. Indeed, he won seven heavyweight titles, and he headlined four WrestleManias. Furthermore, Taker faced and defeated virtually every big name from the past four decades. That’s before you get into his 21-0 winning streak at WrestleMania. And of course, there’s his epic character work that makes his Phenom gimmick the greatest of all time.
Therefore, deciding on Undertaker’s best matches is a real challenge. Yes, some are obvious contenders, but there are so many gems that miss out. Consequently, there’s no room on this list for Brock Lesnar, Randy Orton, CM Punk, or Ric Flair. Plus, we don’t get the trio of Hulk Hogan, The Rock, or Stone Cold Steve Austin. Hell, even his American Bad Ass persona receives no love here. But the bar is so high that it’s impossible to omit any of the matches on our rankings. Some have sentimental value; others define entire generations. With all that in mind, then, let’s get to our list of the best Undertaker matches!
Best Undertaker Matches – Top Ten
10. The Undertaker vs. Kane – WWF WrestleMania XIV
We begin our list of the best Undertaker matches with a bout from WrestleMania XIV. So, for months, Undertaker refused to wrestle his brother Kane. But Kane forced Taker’s hand after lighting a casket on fire with UT inside at Royal Rumble 1998. How Taker escaped, we don’t know. But escape he did, and Taker officially accepted Kane’s challenge for a match at WrestleMania. A match that was preceded by Kane famously Tombstoning former baseball player Pete Rose for the very first time.
The match itself is more of a spectacle than anything. The story built for almost a year, beginning with Paul Bearer’s initial teases of a secret. Therefore, just seeing Taker and Kane do battle was memorable enough. We still get some big moments, though, such as Kane kicking out of two Tombstones before succumbing to the third. Okay, so it lacks the excitement of some of Taker’s more significant matches. But you couldn’t run a list on the Dead Man without featuring his brother Kane.
9. The Undertaker vs. Bret Hart – WWF SummerSlam 1997, WWF Championship Match
Next on our list of the best Undertaker matches is the main event of SummerSlam 1997. Undertaker was the WWF Champion, with anti-American Bret Hart as the adversary. Hart declared that he would never wrestle in the United States again if he lost. But with his longtime enemy Shawn Michaels as special guest referee, surely the Hitman was going down to the Dead Man?
Not necessarily. Because Hart ducked a Michaels chairshot that ended up clobbering Undertaker for the decisive three-count. This is quite a moment because it sows the seeds for the chaotic autumn of 1997 in the WWF. This ranges from Hell In A Cell to Kane’s debut (more on that shortly) to Montreal. But along the way, we get an outstanding back-and-forth match that meshes two varying wrestling styles in a compelling manner. It’s not as flashy as other entries on this list, but you should definitely check out this memorable match.
8. Batista vs. The Undertaker – WWE WrestleMania 23, World Heavyweight Championship Match
Number eight on our best Undertaker matches list comes from WrestleMania 23. And it comes in a somewhat unlikely form: a big-man match where the opponent doesn’t really fear Undertaker. That is Batista, the then-reigning World Heavyweight Champion whose stock was high on SmackDown. The Animal was one of the first truly credible threats to the Streak. Taker, meanwhile, was more focused on becoming World Heavyweight Champion, having earned his opportunity by winning the 2007 Royal Rumble.
On the night, the two powerhouses came at each other hell for leather. Batista established control with a running powerslam through an announcer’s table. Back in the ring, Batista survived a Chokeslam to nail Taker with a spinebuster and Batista Bomb. But Taker rallied long enough to hit a Tombstone for the win and to go 15-0 at Mania. It lacks some of the near-falls that subsequent Streak matches would have. But from start to finish, this is a thrill to watch. And while it only ranks #8 for Taker, it’s certainly one of the very best matches of Batista’s career.
7. Kurt Angle vs. Taker – WWE No Way Out 2006, World Heavyweight Championship Match
Undertaker is most notable for his character work and intimidating aura. But he could hold his own in a straight wrestling match with a compatible opponent. One such adversary was Kurt Angle, and at No Way Out 2006, they delivered a splendid wrestling match. At the time, Taker was just starting to rediscover his mojo for amazing in-ring performances. Angle, meanwhile, was about to enter a troubling period that resulted in his WWE departure. But on this night, the stars aligned to allow the two Hall Of Famers to produce an outstanding match.
The story was that Angle wasn’t afraid to take the fight to Taker. This allowed him to hit the Dead Man with an Angle Slam through an announcer’s table. Not to mention a consistent submission-based attack via the Ankle Lock. But Taker recently rediscovered the Triangle Choke, a basic yet effective counter to Angle’s submission offence. But Kurt outsmarted Taker by cradling Taker whilst trapped in the Triangle, ensuring a fortunate three-count. Taker told Angle afterwards, “I’ve got your number.” A subsequent SmackDown rematch was inconclusive, but here, Kurt was just about triumphant over Undertaker. Regardless of the result, this is a true classic that features on any list of the best Undertaker matches.
6. Edge vs. The Undertaker – WWE WrestleMania XXIV, World Heavyweight Championship Match
It’s back to WrestleMania for a bout that just misses out on the five best Undertaker matches. So, Edge had cashed in Money In The Bank at Taker’s expense in May 2007. After numerous injuries and other twists and turns, we arrived at the destination: WrestleMania XXIV, Edge vs. Undertaker. The World Heavyweight Title was at stake, as was the coveted Streak. More interestingly, though, Edge was also undefeated in singles competition at Mania, giving him a real chance of scoring a major upset.
That he did not. But he did provide us with a career performance on the biggest stage possible. He and Taker slowly but surely craft a flawless match filled with counters, big moves, and close near-falls. Whereas nowadays we see piledriver kick-outs on free TV, here the most primitive reversals achieved the most drama. Mind you, the best near-falls come when a sprinting Charles Robinson almost counts three for Taker off a Tombstone. Not forgetting Taker kicking out of a Spear which convinced many fans to have ended the Streak. But Taker reversed a second Spear into the match- and title-winning Hell’s Gate. I highly recommend this match if you’ve never seen it before.
Best Undertaker Matches – Top Five
5. Undertaker vs. Triple H – WWE WrestleMania XXVIII, Hell In A Cell Match
So, let’s get into the five best Undertaker matches with a truly epic encounter. Now, WWE called this the “End Of An Era”. It wasn’t really, but it was an incredible spectacle to (sort of) conclude a lengthy storyline. HHH tried and failed to defeat Taker at WrestleMania XXVII, but inflicted enough injury for Taker to leave with assistance. This angered the Dead Man enough to demand a rematch at WrestleMania XXVIII. HHH declined, but Taker pushed the issue by suggesting that HHH was inferior to Shawn Michaels. The Game accepted the match, pride bursting through his veins, but only inside Hell In A Cell. Michaels was declared the special guest referee to add more drama.
On the night, Taker initially established dominance, until HHH rebounded with a plethora of chairshots. To prevent Michaels from calling off the match, Taker trapped Shawn in Hell’s Gate; HHH broke this with a sledgehammer. Moments later, Taker somehow kicked out of a Sweet Chin Music/Pedigree combo. By the final moments, HHH was almost broken but took a final sledgehammer shot and a second Tombstone. Taker was 20-0 at WrestleMania, and all three shared an embrace at the top of the stage. It was a magical moment and one that remains powerful viewing to this day.
4. The Undertaker vs. Shawn Michaels – WWE WrestleMania XXVI, Streak vs. Career Match
It’s the first of Shawn Michaels’ three appearances on this list of the best Undertaker matches. I normally avoid highlighting opponents multiple times on these lists. But that’s hard to avoid when the match quality is so high. Even this encounter from WrestleMania XXVI would rank #1 on virtually anybody else’s list. Especially due to the pre-match storyline, with Michaels desperate to have another chance at ending The Streak. After shenanigans galore, Taker agreed to the match, under one condition: Shawn’s career was at stake too. Michaels: “You don’t get it. If I can’t beat you at WrestleMania, I have no career! You’re on!”
This rematch from WM 25 is a work of art. Michaels comes out of the blocks quickly, decisively, and dangerously, as he targets Taker’s left leg. The Phenom rebounds with big moves, but a ringside superkick allows Shawn to moonsault Taker through an announcer’s table. Back in the ring, it’s Sweet Chin Music for one … two … no! Taker kicked out and responded with a Chokeslam/Tombstone combo, only for Shawn to survive. Taker shouted, “Stay down!” A defiant Shawn instead slapped Taker. That led to a jumping Tombstone for an explosive finish and the end of Michaels’ career. This match was masterful and is an absolute necessity to watch.
Best Undertaker Matches – Top Three
3. The Undertaker vs. Shawn Michaels – WWF In Your House XXVIII: Badd Blood, Hell In A Cell Match
So, the original Hell In A Cell match is an all-time classic. Indeed, Taker and Shawn Michaels delivered the template for a near-perfect cage match at Badd Blood 1997. Their rivalry was compelling stuff, and WWF officials decided to lock both men inside steel surroundings. But not just a typical cage; this was Hell In A Cell, a brand new structure. It was 16 feet high, with a roof on top. And the match made its way out of the Cell and onto the roof. From there, Taker destroyed a bloody Michaels, sending him flying off the side of the cage through a table. Back in the ring, Taker almost smashed Shawn’s head entirely with a brutal steel chairshot. But then …
Suddenly, the lights went out, and Paul Bearer arrived with Kane, Taker’s younger brother. Bearer teased the Phenom about Kane’s existence for months, and here he was. Taker and Kane’s first square-off is a moment in itself, and Kane would then Tombstone his older sibling. A crimson-masked Michaels then meekly crawled over to make the three count. What an amazing experience, and one of the absolute highlights of the Attitude Era. You couldn’t write a list of the best Undertaker matches without this battle.
2. The Undertaker vs. Mankind – WWF King Of The Ring 1998, Hell In A Cell Match
In terms of notoriety, this is certainly the most famous entry on our list of the best Undertaker matches. His Hell In A Cell clash with Mankind is one for the ages and one that WWE could never top. Not least because the violence was so insane that the company could never place a performer’s safety at such risk again. Even if it was Mick Foley’s idea to start the match on top of the structure, and to take two iconic bumps. The first of these sees Mankind plummet towards and through the Spanish announcer’s table. That alone should have ended his night, if not his career, and just moments into the contest.
But instead, after a lengthy treatment at ringside, Mankind climbed back up the cage. Moments later, Taker had Chokeslammed him straight through the roof and into the ring below. Note that Foley’s (second) big bump was meant to arrive a few minutes later. Instead, the cage gave way, and Foley was knocked unconscious while somehow also narrowly avoiding grave injuries. Amazingly, the match continued, and Mankind would take two thumbtack bumps (a WWF/WWE first) before finally losing to a Tombstone Piledriver. This is must-see stuff from King Of The Ring 1998. And it’s one of the most legendary WWE matches of all time. But it’s not Taker’s best bout …
Top Ranking – Best Undertaker Matches
1. The Undertaker vs. Shawn Michaels – WWE WrestleMania 25
Taking the top spot of our “Undertaker best matches” list is … well, it’s not a surprise, is it? Of course, The Undertaker’s best match is his showdown against Shawn Michaels at WrestleMania 25. So, in early 2009, Michaels focused on ending Taker’s vaunted WrestleMania Streak. Michaels is Mr. WrestleMania, after all. A significant advantage for Shawn was knowing that he was undefeated against Taker in major singles matches. Furthermore, Shawn maintained a psychological edge over a master of mind games. Going into WrestleMania 25, everybody expected a classic match, but the bout ended up exceeding sky-high expectations.
Indeed, both of these legends delivered a contender for the greatest match of all time. For 30 minutes, they rocked Reliant Stadium with so many big moves and dramatic moments. I will say that I actually personally prefer their rematch at WM XXVI. And that’s partly because of Taker almost breaking his neck at Mania 25 with a dive gone wrong. However, he and Shawn rebounded to deliver an unbelievable sequence of near-falls. Taker’s expression of shock when Shawn withstood a Tombstone Piledriver is just as memorable as the kick-out itself. In the end, Taker hit a second Tombstone for the win, and to go 17-0 at WrestleMania. A truly iconic encounter and the only option to round off our list of the best Undertaker matches.
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So, those are our thoughts on the best Undertaker matches. But what do you think? Let us know by leaving a comment below!