On Sunday 22nd November, 2020, WWE celebrated not just the 34th edition of Survivor Series, but the official retirement of The Undertaker. The show ended with ‘The Dead Man’ saying goodbye on the 30th anniversary of his debut. One of the most iconic characters in WWE history, his transition from the early days of the undead, through the era of the Dark Satanist, past the times of biker brawler and back to a ‘Phenom’, showed both his creativity and longevity.
His first decade mainly consisted of no selling and terrifying heels galore, but the second decade allowed him to expand his game, incorporating mat skills and more prominent selling. Because of this, his best matches often feature in the latter part of his career, but what classics they are.
In celebration of his thirty years, let’s look at fifteen of the best Undertaker matches of all time. You’ll likely notice a theme developing as we look through history.
1. WWF In Your House: Badd Blood (1997)
Hell In A Cell Match | WWF Championship #1 Contender ship
The Undertaker vs. Shawn Michaels w/ Rick Rude, Triple H & Chyna
By 1997, The Undertaker had already been WWF Champion twice, first in 1991, and then earlier that year. He lost the championship to Bret ‘The Hitman’ Hart at SummerSlam, and blamed guest referee Michaels, leading to the creation of Hell In A Cell. The intentions of the gimmick was to prevent interference from D-Generation X, and raising the stakes even further, the #1 Contendership to the WWF Championship awaited the winner.
At the time, this was the most violent match in WWF history, an engrossing twenty minute affair where The Undertaker basically murdered Michaels. Destroying him inside the ring, against the cell, and off the side of the cage, the inaugural HIAC match set a high standard. After exacting tremendously barbaric vengeance against the ‘Heartbreak Kid’, victory seemed certain until the debut of The Undertaker’s brother Kane occurred. One Tombstone by Kane later, Michaels stole the victory, and wrestling would never be the same again.
2. WWF WrestleMania XIV (1998)
The Undertaker vs. Kane
This match represents several elements of The Undertaker’s career. Firstly, it is likely the best match between the kayfabe brothers, setting a standard they never really matched over the next two decades. Secondly, it was the first time a match featuring The Undertaker was deemed a special attraction at WrestleMania, specifically due to the story being told. Thirdly, it was one of the first occasions that The Undertaker was in peril against Kane, the larger and more dangerous of the two.
The match itself is a classic hoss battle, full of strikes and hard hits, with Kane shockingly kicking out of not one, but two Tombstone Piledrivers. At the time, it was one of the most protected finishers in the world (even Hulk Hogan hadn’t kicked out of it) and elevated the match that bit higher. In the end, a desperate Undertaker hit a third Tombstone to vanquish the demon who had plagued him so far.
3. WWF King of the Ring (1998)
Hell In A Cell Match
Mankind vs. The Undertaker
Quite simply one of the most memorable matches in the history of wrestling. In just seventeen minutes, The Undertaker (who entered the match with a broken foot) and Mankind created history with moments that still resonate today. With Shawn Michaels and The Undertaker setting such a high standard the previous year, Mick Foley’s fear of ‘stinking the joint up’ meant gaining the advice of one Terry Funk. In a moment of inspiration, Funk suggested “starting on top of the cage”.
By the end of the match, Foley had been thrown off the cage through an announce table, and (accidentally) Chokeslammed through the cage into the ring. Both men left the match afterwards to standing ovations for surviving, and the fact that The Undertaker won was inconsequential. Foley was cemented forever in history as one of the toughest human beings in wrestling, and The Undertaker’s mythos gained new levels of terror. However, the biggest achievement is the fact neither died at any point.
4. WWE Vengeance (2002)
Triple Threat Match | WWE Championship
The Undertaker (c) vs. Kurt Angle vs. The Rock
This is the only non-singles match included in this list, but it’s an underrated gem from a weaker period of The Undertaker’s career. Even though the ‘American Badass’ may have had its fans, it was unfortunately corrupted by weight issues and disappointing work rate. However, his transition into the more heelish ‘Big Evil’ slightly improved things, with another strong performance around this time in a Ladder Match against Jeff Hardy.
This match was full of intensity throughout, and a rare opportunity to see three legends participating in a battle for the WWF Championship. Undertaker entered as champion at the time, and even though The Rock claimed the championship, all three put in strong performances. However, Taker’s best performance of the year was being saved for a few months later.
5. WWE No Mercy (2002)
Hell In A Cell Match | WWE Championship
The Undertaker vs. Brock Lesnar (c) w/ Paul Heyman
Brock Lesnar debuted in 2002 and quickly tore through the roster,winning the King of the Ring tournament, destroying Hulk Hogan, and defeating The Rock at SummerSlam for the WWE Championship. As champion, Lesnar was challenged by The Undertaker and a No Contest at Unforgiven followed after the two men couldn’t be controlled. Due to this, SmackDown General Manager Stephanie McMahon (back when she was likeable) announced they’d face off in a Hell In A Cell.
This match is vicious and bloody, Undertaker utilising a cast on his arm to beat Lesnar with, and Paul Heyman even bloodied through the cage. Despite the lack of weapons, apart from the steel steps, this aggressive rivalry left both men battered and bloodied, building to a war. In the end, Lesnar defeated the old lion, and showed that the future was here. At least until 2004, when he left for the NFL.
6. WWE No Way Out (2006)
WWE Championship Match
Kurt Angle (c) vs. The Undertaker
Every now and again, you hear of matches that were good enough to appear at WrestleMania. Here, you have a match that many believe should have featured at WrestleMania 22. At the time, Angle was one of the best in the world, busting out great matches with ease, while The Undertaker was developing his repertoire with an MMA strike and submission style. To the surprise of many, The Undertaker proved himself Angle’s equal.
A psychological masterpiece, Angle’s game plan focused on The Undertaker’s leg, while The Undertaker attacked Angle’s arm in the early sections of the match, preparing for his Triangle Choke. Both wrestlers demonstrated smart tactics and the match is close to flawless in execution. Even more impressively, both men came out of this looking strong with a creative finish that showed Angle’s intelligence and that Taker could beat him. It’s just a shame they never wrestled again.
7. WWE WrestleMania 23 (2007)
World Heavyweight Championship Match
The Undertaker vs. Batista (c)
In 2007, Undertaker made history when he became the first man to win the Royal Rumble from the No. 30 position. With the opportunity to choose what championship to challenge for, SmackDown’s Batista refused to shirk the ‘Deadman’, attacking one another several times. To the surprise of both men, they were booked halfway down the card, a slight that inspired them to prove everyone wrong.
In a fast-paced, physically hardhitting battle, Batista and Taker defied expectations, with a Batista running powerslam through an announce table a special highlight and a nearfall on a Last Ride getting the crowd excited. Power moves galore finished on a massive Tombstone from Taker to win and earn the title. The importance of this match is underappreciated, as it started a sequence of amazing matches at WrestleMania.
8. WWE Backlash (2007)
Last Man Standing Match | World Heavyweight Championship
The Undertaker (c) vs. Batista
After the chemistry displayed at WrestleMania, it was unsurprising to see The Undertaker and Batista face off once again. This time capitalising on the power moves and brawling that excited the crowd last time, they went with a huge Last Man Standing match. A phenomenal battle between two colossal giants from the first minute, brawling around the arena and culminating on the main stage, where a desperate Batista attempted a Spear that sent both men through the stage and unable to answer the count.
While a draw was far from popular at the time, it suited the story, and thirteen years on, it can be appreciated as a standalone fight. Whereas the match against Batista at WrestleMania was the beginning of a renaissance for The Undertaker, this bout confirmed that it wasn’t a flash in the pan. The next seven years featured the majority of The Undertaker’s best matches.
9. WWE WrestleMania XXIV (2008)
World Heavyweight Championship Match
The Undertaker vs. Edge (c)
The following year, The Undertaker became the #1 Contender to the World Heavyweight Championship at No Way Out, challenging Edge in the main event of WrestleMania 24. At the time, both men entered the match undefeated at WrestleMania, with a 15-0 and 7-0 streak respectively, so one streak was going to end. Edge had also previously cost The Undertaker the championship on three occasions, even cashing in the Money In The Bank to take the title himself.
Edge’s intelligence meant that he was prepared for every big Undertaker move, countering them with tricks and reversals, a gradual increase of pace combined with Edge’s focus on ‘Taker’s back telling a great story. Even after all that, The Undertaker survived, taking down Curt Hawkins and Zack Ryder as they interfered for Edge. In the end, after hitting the Spear, a cocky Edge was caught unaware in the Hell’s Gate and tapped out, The Undertaker becoming World Champion once again. An instant classic that doesn’t receive the love it deserves.
10. WWE SummerSlam (2008)
Hell In A Cell Match
The Undertaker vs. Edge
After the tremendous match at WrestleMania, Edge and Undertaker’s feud continued until One Night Stand, where The Undertaker lost a TLC match and was banished from the WWE. Months later after cheating on his fiancée Vickie Guerrero, Edge was punished by Vickie with a Hell In A Cell match against a reinstated Undertaker. This match was the culmination of a sixteen month feud that began when Edge had cashed in on ‘Taker.
An amazing feud capped off with an awesome battle in the Cell, both men utilised tables, ladders, chairs, and television cameras in call backs to their other matches. Reminiscent of the first Cell eleven years previously, Undertaker destroyed Edge, eventually hitting a con-chair-to and a Tombstone Piledriver to win the match. Afterwards, in an emphatic moment full of hellacious intent, Undertaker Chokeslammed Edge off a ladder through the ring.
11. WWE WrestleMania 25 (2009)
Shawn Michaels vs. The Undertaker
Throughout the annals of WrestleMania history, there are very few matches more recognised and remembered than the WrestleMania 25 match between Shawn Michaels and The Undertaker. In a match filled with imagery and symbolism, it opened with Michaels descending from a platform in a white version of The Undertaker’s garb, while Undertaker himself rose from the dark among the fire.
After a terrifying botched suicide dive, the match somehow got even better, as these two legends fought to prove themselves the better man, exchanging finishers and nearfalls. Eventually, Michaels took one chance too many, caught mid-Moonsault by The Undertaker who hit the Tombstone Piledriver for the victory. A match that critics and fans alike have rained plaudits upon, it is a must-see for any fan.
12. WWE WrestleMania XXVI (2010)
Streak vs. Career
Shawn Michaels vs. The Undertaker
The previous year was an instant classic, but it’s impossible to ignore the sequel the following year. Whereas the first was based on a competitive respect between two legends, this match was full of bitterness and resentment. After winning the 2009 Slammy Award for Match of the Year for the first match, Michaels decreed he could defeat his opponent, and began a descent into madness. His elimination from the Royal Rumble and qualification losses forced Michaels to cost The Undertaker his World Championship. Because of that, Undertaker finally accepted the match with the proviso that if Michaels lost, his career was over.
An emotionally heartbreaking battle unfolded with both men desperate for victory. A resistant Michaels refused to stay down, but The Undertaker eventually proved too much, an impactful Jumping Tombstone Piledriver finally killing the last fight in Michaels. With Michaels gone, the streak reached 18-0, and fans were left to lament the end of a tremendous career, but regale in the perfect ending for the ‘Heartbreak Kid’.
13. WWE WrestleMania XXVII (2011)
No Holds Barred Match
Triple H vs. The Undertaker
For the fifth year in a row, The Undertaker featured in the best match on the card, this time battling Michaels’ best friend Triple H. They had actually fought at WrestleMania X-7, but this match had the context of revenge for Michaels, the possibility of Triple H besting Michaels’ achievement, and the continued transition of ‘Taker into a part-time role.
A much more physical and difficult match for Undertaker, the two men used the lapsed rules to their advantage, brawling on the outside. Between Spinebusters through the announce table, the use of chairs, and Pedigrees galore, the possibility of Undertaker losing felt real. However, akin to his match against Edge several years previously, Undertaker took advantage of a relaxed Triple H to lock in the Hell’s Gate, getting the submission victory to increase his streak to 19-0.
14. WWE WrestleMania XXVIII (2012)
Hell In A Cell Match
Triple H vs. The Undertaker
Despite his victory the previous year, The Undertaker had to be assisted from the ring due to being unable to walk and was on hiatus until the following January. In a rare role reversal, Undertaker challenged Triple H, his victory tainted by the aftermath. After calls of cowardliness from Taker, the rematch was finally accepted, this time in a Hell In A Cell match with Shawn Michaels as the referee.
The importance of this match was unquestionable with legendary commentator Jim Ross brought back especially, billed as “the end of an era”. Triple H brought in steel chairs, steel steps, and even a sledgehammer in an attempt to get the victory, with one of the closest nearfalls ever after a Sweet Chin Music and a Pedigree combo almost defeated ‘The Phenom’. Against the odds, Undertaker finally laid Triple H to rest, his streak extended to 21-0. In an iconic moment, all three embraced at the entrance, the closing chapter of the Michaels-Undertaker-HHH story.
15. WWE WrestleMania 29 (2013)
CM Punk vs. The Undertaker
By 2013, The Undertaker’s Streak was renowned as truly special, the possibility of defeating The Undertaker at WrestleMania at times felt bigger than any championship match. In 2013, The Undertaker offered an open challenge, with Punk, Randy Orton, Big Show and Sheamus all wanting a shot at ending the Streak. A Fatal Four-Way ended with Punk gaining victory and earning the chance to challenge ‘Taker. Unfortunately, the passing of Paul Bearer during that period was used in a tasteless angle, Punk and his manager Paul Heyman taunted the death of Undertaker’s former friend and manager.
Thankfully, the match itself was another WrestleMania classic from ‘Taker. Punk used his smarts and youthful exuberance to defy everything Undertaker had, making the crowd believe he might succeed. This big match concluded with The Undertaker reversing a GTS into a second Tombstone Piledriver for the victory, reaching 22-0. At the time, nobody could have guessed it was the last time The Undertaker’s undefeated streak would survive.
Over the last thirty years, The Undertaker has created many memories for audiences around the world, a figurehead for generations, and a true locker room leader. While his more recent work hasn’t been to his highest standard, nobody can dispute the quality he has produced. As we witness the retirement of a legend from the upper echelons of the wrestling world, let’s rejoice in the classics he has left us in years gone by.
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