The Undertaker’s Best WrestleMania Matches of All Time

The Undertaker vs. Triple H (WrestleMania XXVIII)

No wrestler is as closely tied to WrestleMania as the Undertaker. Headlining WWE’s hallmark pay-per-view on more than one occasion, the Undertaker has been featured in some of wrestling’s all-time classic matches showcased on the “grandest stage of them all.”

Making his first WrestleMania appearance at WrestleMania VII in 1991, the Undertaker became one of the PPV’s foremost attractions, thanks mainly to his legendary undefeated streak that lasted just over 20 years.

Known simply as “the Streak,” challengers far and wide tried hard to score a win over the Dead Man, only to be met by inevitable failure time and time again. Even when the Undertaker’s Streak finally came to a close (courtesy of Brock Lesnar in 2014), the Undertaker still had an array of rich matches forever attached to his name.

When looking at the spectrum of the Streak, it’s clear that some of the Phenom’s WrestleMania matches were far better than others. From his matches against fellow legends like Shawn Michaels and Triple H to rising stars like Randy Orton, Batista, and CM Punk, here are some of the greatest WrestleMania matches to feature the Undertaker.

1. The Undertaker vs. Shawn Michaels (WrestleMania XXV)

The Undertaker vs. Shawn Michaels (WrestleMania XXV)
Image Credit: WWE.

Shawn Michaels’ bout with the Undertaker at WrestleMania XXV not only has the distinction of being either man’s best WrestleMania match-up — it’s also one of the single greatest professional wrestling matches of all time.

Beating Vladimir Kozlov and earning a right to challenge the Phenom at WrestleMania, Michaels looked to make history, putting his born-again Christian values against the demonic presence of the Undertaker. Surpassing storylines alone, the match also reignited the excellent 1997 feud between Taker and Michaels and their epic standoffs at the 2007 and 2008 Royal Rumble events.

In retrospect, no two athletes were as iconic as the Heartbreak Kid and the Demon of Death Valley, both men serving as staples of WWE programming throughout the Attitude Era and Ruthless Aggression Era. So naturally, there was a lot of hype surrounding the bout, but both men surpassed expectations, delivering the finest match in WrestleMania history.

2. The Undertaker vs. Shawn Michaels (WrestleMania XXVI)

The Undertaker vs. Shawn Michaels (WrestleMania XXVI)
Image Credit: WWE.

In the 2010 rematch between Michaels and the Undertaker, what set WrestleMania XXVI apart from its predecessor was the utterly fantastic storyline moving into the match. Sensing that he had come exceptionally close to beating the Dead Man and breaking the Streak, Michaels slowly became obsessed with challenging the Undertaker to a rematch — a challenge Taker promptly refused, claiming a second bout would only lead to more disappointment for HBK.

Consumed by his growing need to break the Streak, Michaels spent the early portion of 2010 pining after the Undertaker, coming close to winning the 2010 Royal Rumble match (earning a title match against Taker) and costing Taker the World Heavyweight title at the Elimination Chamber pay-per-view. Infuriated, the Undertaker finally accepted Michaels’ challenge, with the added caveat that, should Michaels lose, he would be forced to retire (echoing the stipulation in Michaels’ match against Ric Flair at WrestleMania XXIV).

While their initial 2009 match was only marginally better, the storytelling behind the bout was fantastic. As with all the best wrestling matches, each man told a story in the ring, fueled by Michaels’ desperation to retain his career and the Undertaker’s desire to protect his Streak.

3. The Undertaker vs. Triple H (WrestleMania XXVIII)

The Undertaker vs. Triple H (WrestleMania XXVIII)
Image Credit: WWE.

In 2011, Triple H and the Undertaker had an incredibly entertaining match at WrestleMania XXVII, with Undertaker just barely managing to score a win over the Game. Needing to be assisted to the backstage area following the match, Undertaker had a rare score to settle in time for WrestleMania XXVIII.

Looking to prove he still had what it took to defend his Streak, the Undertaker challenged Triple H, reversing the same approach WWE had taken with Michaels versus Undertaker II at WrestleMania XXVI. Reluctantly agreeing to face the Dead Man once again, the clash was officially booked to take place inside the Cell (a specialty match for both competitors), and with Triple H’s best friend/Undertaker’s respected rival, Shawn Michaels, acting as special guest referee.

Triple H and Undertaker’s clash at WrestleMania XXVIII was purely phenomenal and filled with near falls, devastating finishers, and chair shots galore. Described by WWE as the “End of an Era,” everyone involved in this match managed to tell an emotional story. Triple H may have lost, but all three men came out looking like winners, even if one had already retired for just over two years.

4. The Undertaker vs. Edge (WrestleMania XXIV)

The Undertaker vs. Edge (WrestleMania XXIV)
Image Credit: WWE.

After winning the World Heavyweight Championship from Batista at the previous year’s WrestleMania, the Undertaker set out to see if lightning would strike twice at 2008’s WrestleMania XIV. As with most entries on this list, the thing that made this match so great was the storytelling involved in it.

For the past year, the Undertaker had been engaged in a brutal feud with the Animal, Batista, a rivalry that had lasted throughout most of 2007. Edge was continuously throwing himself into the mix, the Ultimate Opportunist who had used his on-screen romantic attachment to SmackDown general manager Vickie Guerrero to integrate himself in the world title picture.

Using Guerrero’s corrupt authority to his advantage (along with his dedicated stooges, The Edgeheads), Edge was a very different threat to the Undertaker’s Streak — albeit a formidable one at that. At several points, it seemed that the Rated-R Superstar would be the first to finally score a pinfall over the Undertaker, only for a sudden Hell’s Gate submission hold to end Edge’s World title reign and secure another win for the Undertaker.

5. The Undertaker vs. Triple H (WrestleMania XXVII)

The Undertaker vs. Triple H (WrestleMania XXVII)
Image Credit: WWE.

At WrestleMania XXVI, the Undertaker delivered one of the finest matches of his career against Shawn Michaels, ending the Heartbreak Kid’s career in a certified classic. One year later, Michaels’ DX stablemate Triple H set out to accomplish what his best friend couldn’t, avenging Michaels’ loss and beating the Undertaker where it mattered most: WrestleMania XXVII.

Packaged as a no-holds barred match, the Undertaker versus Triple H was single-handedly the best match at 2011’s WrestleMania. Using the lack of rules to the full extent imaginable, Taker and Triple H battled around the ring and adjoining area, crashing through announce tables, into the steel steps, and even through Michael Cole’s custom “Cole Mine” glass box.

Compared to their later, more emotional encounter at WrestleMania XXVIII, Triple H and the Undertaker’s second WrestleMania match felt much more raw and savage. Between the stiff shots, the hard blows from the steel chair (including an unsanctioned shot to the head), and the ridiculous bumps each man took, the whole match seemed like a genuine struggle that both wrestlers were trying hard to survive.

6. The Undertaker vs. CM Punk (WrestleMania 29)

The Undertaker vs. CM Punk (WrestleMania 29)
Image Credit: WWE.

After repeated back-to-back matches against Shawn Michaels and Triple H at four consecutive WrestleManias in a row, the Streak’s first brand-new challenger in years came in the form of CM Punk. Fresh off his lengthy reign as WWE Champion and still at the height of his popularity, Punk set his sights on the Streak after losing the title to a returning Rock.

With Paul Heyman in his corner, Punk spent weeks leading up to WrestleMania 29 mentally toying with the Undertaker, insulting the memory of his recently departed manager, Paul Bearer, by making away with Bearer’s signature urn. Enraged by Punk’s lack of respect for Bearer, the Undertaker accepted Punk’s challenge, setting the stage for this match.

The build-up behind the feud may have been controversial, but there’s no question the actual match was anything but fantastic. In plain respect, it was clear from the booking that Punk never had a serious chance of breaking the Streak, but there were more than a few moments where it seemed that he’d pull a surprise victory over Taker. The final entry in the Undertaker’s mythic Streak was also the last truly great match in the Undertaker’s historic career.

7. The Undertaker vs. AJ Styles (WrestleMania 36)

The Undertaker vs. AJ Styles (WrestleMania 36)
Image Credit: WWE.

The Undertaker’s WrestleMania 36 match against AJ Styles is unique for several reasons. Most notably, it’s the only match featured here where the Undertaker’s Streak had long since ended, the Undertaker having been beaten by Brock Lesnar six years prior. It’s also the final WrestleMania match in the Undertaker’s career, bringing his final WrestleMania tally to two losses and 24 victories (25 with the defeat of AJ Styles here).

Winning the Tuwaiq Mountain Trophy out from under Styles, an addled Phenomenal One spent the opening months of 2020 mocking the Undertaker, delivering threats and insults that grew more and more personal with time. Then, in retaliation, the Undertaker cost Styles his match against Aleister Black at Elimination Chamber, laying the groundwork for their encounter at WrestleMania 36.

Thankfully, WWE learned from their mistakes with this match-up. Realizing how much the Undertaker had slowed down in recent years and taking advantage of the lack of crowds at WrestleMania 36 (because of the pandemic), the company filmed the horror-film-like showdown between Styles and Taker as the first-ever Boneyard Match. The resulting bout was unlike another in the Undertaker’s career, sending the Phenom out on a blessedly high note.

8. The Undertaker vs. Randy Orton (WrestleMania 21)

The Undertaker vs. Randy Orton (WrestleMania 21)
Image Credit: WWE.

In early 2005, WWE had reverted Randy Orton to his former Legend Killer persona after his breakthrough feud with Evolution leader Triple H. Targeting some of the most iconic wrestlers in WWE, it was only natural that Orton goes after the Undertaker, culminating in several methodical attacks on Orton’s on-screen girlfriend, Stacy Keibler, and the Undertaker’s former rival, Jake Roberts.

Backed by his father, “Cowboy” Bob Orton, the young Legend Killer met his match at WrestleMania 21, biting off more than he could chew when facing the Undertaker. But, for as many hits as he took, Orton proved a lot more wily than anyone might’ve thought possible, demonstrating the same keen resiliency that elevated him to the top of WWE in 2004.

As strong as the overall match was, two key moments continue to define this bout: first, Randy Orton’s incredible counter from a chokeslam into an RKO mid-air, as well as the Undertaker managing to reverse Orton’s Tombstone into a piledriver of his own, ending the match and ensuring the Streak lived on.

9. The Undertaker vs. Batista (WrestleMania 23)

The Undertaker vs. Batista (WrestleMania 23)
Image Credit: World Wrestling Entertainment, Inc.

Achieving another career accolade by winning the 2007 Royal Rumble, the Undertaker could choose the world champion he wanted to face at WrestleMania 23. Opting for World Heavyweight title holder Batista over ECW Champ Bobby Lashley and WWE Champ John Cena, virtually no one could’ve known they were seeing the start of 2007’s best feud when the Undertaker officially made his decision.

Breaking out all of their most hard-hitting signature moves, the Animal versus the Phenom proved to be one of the most intensely physical matches in any man’s career at that point. However, between the Undertaker’s resiliency, veteran wrestling knowledge, and Batista’s brute strength, the two were an unexpectedly great pairing, developing natural chemistry whenever they stepped foot in the ring together.

The first of several matches between Batista and Undertaker, this match pretty much set the standard for every one of Undertaker’s Streak matches that came after (every single one of which appears on this list).

10. The Undertaker vs. Triple H (WrestleMania X-Seven)

The Undertaker vs. Triple H (WrestleMania X-Seven)
Image Credit: World Wrestling Entertainment, Inc.

Just because the Undertaker and Triple H’s later WrestleMania encounters rank above their first match at WrestleMania X-Seven doesn’t mean this match isn’t great in its own right. In many respects, it may be the best of the Undertaker’s WrestleMania matches during WWE’s Attitude Era.

Sure, WrestleMania XIV’s Kane versus the Undertaker benefited from some strong storylines, and Ric Flair versus the “Big Evil” Undertaker at WrestleMania X8 was surprisingly entertaining. Still, Triple H’s initial WrestleMania clash with the Undertaker was pure anarchic, Attitude Era fun.

Knocking out the referee halfway through the match, it was only a matter of moments before Taker versus Triple H I descended into full-on chaos. Fighting through Houston’s Astrodome, Triple H and Undertaker chased each other through the crowd, around the staging area, and back to the ring, ending with an unexpected Last Ride out of the corner. To this day, it’s an underrated gem among Undertaker’s WrestleMania performance list, existing side by side with other overlooked matches like Taker v. Flair, Taker v. Jake Roberts, and Taker v. Diesel.

This post was produced and syndicated by Wealth of Geeks.

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Richard Chachowski is an entertainment and travel writer who has written for such publications as Wealth of Geeks, Looper, Screen Rant, Fangoria, and Sportskeeda, among many others. He received his BA from The College of New Jersey and has been a professional writer since 2020. His geeky areas of interest include Star Wars, travel writing, horror, video games, comic books, literature, and animation.

Richard has been an avid consumer of movies, television, books, and pop culture since he was four-years-old. Raised on a diverse mix of Clint Eastwood Westerns, Star Wars, sci-fi and horror films, Alan Moore comics, and Stephen King novels, he eventually turned his various passions into a creative outlet, writing about film, television, literature, comics, and gaming for his high school and college newspapers. A traveling enthusiast, Richard has also managed to create a career out of journeying abroad, venturing to such awe-inspiring places as the Sonoran Desert of Mexico, the rainforests of Costa Rica, and the scenic coastline of Haiti. Upon graduating from TCNJ, Richard set his sights on a career in journalism, writing extensively about the art of traveling and the entertainment medium for various online publications. When he’s not busy making his way through The Criterion Collection, he can be found either reading or planning a trip somewhere (preferably someplace with a scenic hiking trail).