The Undertaker’s Streak: A Deep Dive Into Every WrestleMania Victory

The Undertaker, also known as The Phenom, may be one of the most iconic figures in the history of professional wrestling. A career over three decades in the industry has more to do with his numerous accolades, unforgettable matches, and a legacy that can justly be regarded beyond the sport. Perhaps the most notable part of The Undertaker’s career would be his seemingly unbreakable winning streak at WrestleMania, simply referred to as “The Streak.” Starting with his debut at WrestleMania VII in 1991, The Streak lasted through his twenty-first win at WrestleMania 29 in 2013. That would be the ultimate stamp in the annals of history for the sport. This paper takes us inside each win that configured The Streak, its context, opponents, and impact of these monumental matches.

WrestleMania VII: The Beginning of The Streak

Opponent: Jimmy “Superfly
He debuted at WrestleMania on March 24, 1991, and piled it out with the legendary Jimmy “Superfly” Snuka. At that point in time, The Undertaker was pretty fresh in World Wrestling Entertainment, as he had just debuted a few months earlier at the 1990 edition of the Survivor Series. Although a rookie, he was already creating a storm with his dark and mysterious character and his greater intimidating presence.
The Undertaker overwhelmingly won this match against Snuka, showing all of his big moves, including the Tombstone Piledriver, in virtually five minutes. IT was a portend of things to come of the featuring star’s monumental winning streak at the marquee annual event for the WWE.

WrestleMania VIII: A World Champion Defends His Honor Against Jake “The Snake” Roberts

Rival: Jake “The Snake” Roberts
On April 5, 1992, The Undertaker faced Jake “The Snake” Roberts at WrestleMania VIII. Who needed no introduction—a legend in his own light, quite possibly one of the greatest psychological warriors of wrestling. The point is that this was The Undertaker’s second appearance at WrestleMania, and at that stage, he challenged one of the most sinister characters that WWE fans had ever known.
The storyline would lead up to Roberts attempting to manipulate The Undertaker and Paul Bearer but ultimately finding out that The Phenom was immune to his tactics. The result was listed as The Undertaker had defeated Roberts, and therefore The Deadman came back again as an unbeatable figure throughout WWE, with the Tombstone Piledriver ending another rivalry.

WrestleMania IX: Giant Gonzalez Showdown

Opponent: Giant Gonzalez
WrestleMania IX, April 4, 1993, delivered the ultimate test for The Undertaker as he stood opposite the towering Giant Gonzalez, well over the remarkable height of seven feet. The storyline that included the Giant Gonzalez told of his manager, Harvey Wippleman, wanting retribution because The Undertaker had messed up things and vanquished his old set of clients.
The spectacle was the match itself, which took place during an outdoor event at Las Vegas’s Caesars Palace. It was more a bout of spectacle than technical; the highly overpowered sheer size of Gonzalez made The Undertaker take away the win by the conscious disqualification of Gonzalez from use of chloroform. So controversial was the finish not to kill The Streak but in a very odd fashion.

WrestleMania X: The Deadman’s Reign Unwritten

No-show at WrestleMania X
The Undertaker was not involved in action back at WrestleMania X in 1994. Well, after a Casket Match at the 1994 Royal Rumble event, against Yokozuna, The Undertaker was buried so he had time to heal and take time off. Everything did not stop, because even though this wrestler was not in the event, his legend grew bigger with the fans.

WrestleMania XI: The Phenom vs. King Kong Bundy

Rival: King Kong Bundy
The Undertaker made his lone appearance of the year on April 2, 1995, returning to WrestleMania for WrestleMania XI to renew his feud with the members of the Million Dollar Corporation, this time King Kong Bundy. He tried to interfere on the behalf of diabolic love, but The Undertaker withstood all that came in his way, thereby outlasting the other in good form. The match was power-packed with moves and lots of gimmickry, and right at the finish, he delivered a flying clothesline.

WrestleMania XII: A Grudge Match with Diesel

Opponent: Diesel
The year was 1996, and on March 31, The Undertaker was wrestling Diesel a.k.a. Kevin Nash during the professional fighting event WrestleMania XII. Their enmity had been fanned through Diesel’s interference in The Undertaker and vice versa in his matches.
The match had been a slugfest, implicitly telling of the power and tenacity of each competitor. In the end, though, The Undertaker nailed a Tombstone Piledriver to secure his fifth-straight WrestleMania. And his reputation will grow further; come hell or high water, The Undertaker is always there when the match truly counts.

WrestleMania 13: The Championship Challenge vs. Sycho Sid

Opponent: Sycho Sid
At the Grand Daddy of ’em All, on March 23, 1997, at WrestleMania 13, The Undertaker had a shot at wrestling the WWE Champion; he challenged the reigning champion, Sycho Sid.
To the hard fight, full of heat and struggle, which seemed to be the main event, a match continued. The Undertaker never relented on his fierce desire to win back the WWE Championship, exhibiting more of his resilience. The grudged Bret Hart’s inference, the still hold of final Tombstone Piledriver deliverance upon Sycho Sid, and The Undertaker won the WWE Championship, extending The Streak to 6-0.

WrestleMania XIV: A Brotherly Feud with Kane

Rival: Kane
One of the most remembered and emotionally high matches in The Undertaker’s entire WrestleMania saga was on March 29, 1998, against his storyline brother, Kane. This match was full of supernatural overtones and comfortably settled into the storyline-heavy proceedings laden with betrayals and family dramas.

Kane had brutalized The Undertaker ahead of time and was making all sorts of threats to finish off The Undertaker. And after all those tribulations – both emotional and physical – The Undertaker wins the match by hitting three turnstile Piledrivers in succession on his giant sibling. This match pushed The Streak to 7-0 and would settle the myth that was the entire sibling rivalry deal all at once.

WrestleMania XV: Hell in a Cell against Big Boss Man

Antagonist: Big Boss Man
At WrestleMania XV on March 28, 1999, The Undertaker fought Big Boss Man in a Hell in a Cell match. In a long line of actions, this fight was part of The Undertaker’s “Ministry of Darkness” phase, and it premiered in its degree of darkness and sinister roles.
The match was brutal and unforgiving, where both opponents made good use of the steel cage structure. Eventually, The Undertaker sealed it with a Tombstone Piledriver, and yet another controversial and shocking element bound with post-match antics, including the hanging of Big Boss Man, relates this to the victory as his first in the Streak, bringing it to 8-0.

WrestleMania 2000: Not Appearing

Injury
The Undertaker was absent from WrestleMania 2000 due to a groin injury, which required surgery. The fans missed him, yet the anticipation for his return grew bigger. The Phenom used his absence to rest and returned with a new rejuvenated outlook on life.

WrestleMania X-Seven: A Biker vs. Triple H

Adversary: Triple H
The Undertaker returned to the sport of wrestling on April 1, 2001, at WrestleMania X-Seven against Triple H. The bout made The Undertaker align with his human avatar, recognized as the “American Badass”, renouncing his somber supernatural elements and becoming a biker.
An absolute brawl saw these two competitors fighting all over the arena in that match. Despite all allegations and interference from the referee, other wrestlers, Triple H, and what have you, he still drove himself in through a Last Ride powerbomb at the end. This victory expanded The Streak to 9-0 and showed just how agile and adaptive The Undertaker was in the ring.

WrestleMania X8: An Encounter With Ric Flair

Rival: Ric Flair
It was during WrestleMania with the date March 17, 2002. The Undertaker fought in a no-disqualification match against the legendary Ric Flair. There seemed to be a personal approach regarding the match buildup as The Undertaker seemed to gun after the Flairs, including his family. The whole match was hard with both opponents utilizing weapons and their surroundings. Nonetheless, Arn Anderson and others interfered many times leading to a win in favor of The Undertaker by a Tombstone Piledriver, taking The Streak to 10-0 and keeping him in such a status until today in WrestleMania.

WrestleMania XIX: Handicap Match vs. Big Show and A-Train

Opponents: Big Show
At WrestleMania XIX, dated March 30, 2003, The Undertaker competed in a Handicap match against Big Show and A-Train. This was an exception to his usual singles competition.
Although greatly outnumbered, The Undertaker would, through interference from his own Equalizer Nathan Jones, overcome the odds and carry the win. The poor wrestling performance ended with A-Train receiving a Tombstone Piledriver from The Undertaker, bringing The Streak to 110.

WrestleMania XX: The Homecoming of The Deadman

Opponent: Kane
Parade continued at its normal speed from Six Man Hell in a Cell Match to… WrestleMania XX, 14th March 2004… Returning back to The Undertaker…”The Deadman” persona, Undertaker engaged in his most awaited rematch with Kane fueling both.
Injected with the supernatural elements and such rife dramatics of matches past, The Undertaker emerged from a casket and re-embraced his original character. Nonetheless, with his very best efforts, The Undertaker managed to put Kane down with a final Tombstone Piledriver, moving The Streak to 12-0 and reimposing himself at the top of the hierarchy within the WrestleMania world.

WrestleMania 21: Randy Orton Collision

Opponent: Randy Orton
On April 3, 2005, at WrestleMania 21, The Undertaker went up against Randy Orton, known by fans as “The Legend Killer.” Orton definitely felt omens that it would be the end of The Streak and would solidify his legacy as one of the top WWE superstars.
But it was after that something special happened in this match; let this be a classic example of an intergenerational fight, where Orton, with all his craft and agility, gave The Undertaker a fight worth a watch. But that wasn’t going to be good enough, and he sure didn’t, for The Streak, with a little help from Orton’s father, “Cowboy” Bob Orton, moved on assuredly to 13-0, thus begging the question: Did the legend really exist?.

WrestleMania 22: The Casket Match against Mark Henry

Rival: Mark Henry
April 2, 2006: The main event of the evening was a Casket Match pitting The Undertaker against Mark Henry. This match was another throwback for taking The Undertaker back to his supernatural roots, along with having that added stipulation of putting the opponent in a casket to win. It really turned into a physical contest, but Henry had been able to dominate much of it with his straight-up power over The Undertaker. The Phenom was not going to be denied, though. He had hit a Tombstone Piledriver and rolled him into the casket. This set the mark for 14-0 on The Streak.

WrestleMania 23: Winning the WWE Title by Def

Opposition: Batista
A WrestleMania 23, April 1, 2007: The Undertaker is standing across from Batista, lying in the center of the ring for the World Heavyweight Championship—really explosive. Those two characters, well pinned, wrestling for strength and intensity, it promised to be. This was quite ruthless and competitive on both parts, as The Undertaker already made some of his personal moves and physiques slowly against Batista. Finally, got the chance to execute the very dangerous Tombstone Piledriver and got the pin to capture the World Heavyweight Title and put the record at 15-0.

WrestleMania XXIV: Edge’s Primal Encounter

Rival: Edge
WrestleMania XXIV: The main event match at this one was The Undertaker vs. Edge for the World Heavyweight Championship. For the fact, there was a great build to the match, with Edge vowing to end The Streak, take on The Undertaker right, and leave with the World Heavyweight Championship.

The match was Survivor Series—consisting of a classic WrestleMania main event, with both executing high-impact moves—involving a breathtaking dramatic near-fall. However, in spite of it, The Undertaker forced The Edge to submit with his Hell’s Gate submission hold, becoming the new World Heavyweight Champion, thus running The Streak to 16-0.

WrestleMania 25: The Showdown

Rival: Shawn Michaels
WrestleMania 25 took place on April 5, 2009, showcasing one of the best matches ever produced in WWE history as The Undertaker battled Shawn Michaels. What mattered most in that match was the fact that this was the match that Michaels really wanted to enslave The Streak with his infectious style of cheerleading.

Match storytelling and in-ring performance between both performers were just a masterclass in spectacle delivery forms. Scoring the win after a great series of moves and near-falls, Undertaker delivered a second Tombstone Piledriver to Michaels to score a victory and take the Streak to a mounting 17-0.

WrestleMania XXVI: The Rematch with Shawn Michaels in Career vs. Streak

Rival: Shawn Michaels
WrestleMania XXVI took place on March 28, 2010, featuring a rematch between The Undertaker and Shawn Michaels, this time being a match in which Shawn Michaels put his career on the line. The stakes were even further raised now, with Michaels promising to finally end The Streak or retire from professional wrestling.

It was a classic match—emotion, drama, high-impact moves, all piled on top. The Undertaker finally hit the Tombstone Piledriver to send Michaels to his exit, and The Streak progressed to 18-0. That match really solidified both of those guys’ statuses in history; this match was the true spirit of competition at its finest. This is really, when looking back, billed as one of the all-time matches of World Wrestling Entertainment.

WrestleMania XXVII: The No Holds Barred Match of Triple H

WrestleMania XXVII, which took place in 2011 on April 3, introduced a No Holds Barred wrestling match where The UnderTaker was pitted against Triple H. The whole thing was based on the legendary history between these two people and the mutual respect-versus-rivalry thing. The contest was brutal and very physical, but this time around, they fought with a lot of weapons and with the surroundings in order to get any sort of advantage over each other. No matter, The Undertaker, after taking a lot of punishment, eked out the win with his finishing Hell’s Gate submission move, inching The Streak to 19-0. The match was just a blast of the many qualities of resilience on display by The Undertaker when it comes down to determination.

WrestleMania XXVIII Opponent: Triple H
At WrestleMania XXVIII, on April 1, 2012, The Undertaker fought Triple H in a Hell in a Cell match, where Shawn Michaels was the special guest referee. This match had lastly been dubbed “End of an Era” and indeed was the pinnacle of the long-standing rivalry. The match itself was a battle of epics, with both men providing one of the most brutal, hard-fought battles Shawn Michaels finally got in there with him signifying the drama and emotion of a Hamlet of our times. In the end, The Streak extended to 20-0 with a victory secured when, after hitting a Tombstone Piledriver, The Undertaker sealed his place in the annals of everlasting champions in “The Showcase of the Immortals.”

WrestleMania 29 – Feuding with CM Punk
Last year in April at WrestleMania 29, the world anticipated The Undertaker versus CM Punk. The buildup to this ordeal has, in fact, taken on very personal undertones now, as Punk went a few steps overboard and really ripped into The Undertaker and Paul Bearer. The match turned out to be a classic encounter with both throwing high impact moves and dramatic sequences. Punk was spared almost until the last moment, when The Undertaker delivered the Tombstone Piledriver to win the contest and extend the streak to 21-0, standing with his position as one of the biggest legends in the history of WrestleMania.

WrestleMania XXX—The End of an Era
Opponent: Brock Lesnar

On April 6, 2014, in the main event at this year’s extravaganza, the event known as “The Streak” came to an end: The Undertaker vs. Brock Lesnar fought an absolutely shocking match. Fighting his heart out, The Undertaker was on the receiving end of three straight F-5s by Brock Lesnar, getting the monumental win at 21-1 to end The Streak. This was the moment that trembled across the world of wrestling: The Streak was over and history had been made in the WWE. The Undertaker remains a living legend of The Showcase of Immortals, WrestleMania.

Conclusion
The Streak at WrestleMania is one of the groundbreaking and most fabled records in professional wrestling history. Each victory represents a separate chapter in the book that represents The Undertaker’s illustrious career—testaments to his resilience, ability to adapt, and continued bottomless wellspring of appeal to fans around the globe. From his debut victory over Jimmy Snuka through unforgettable matches with legends like Shawn Michaels and Triple H, The Streak has rocked the world of sports-entertainment. As much as The Streak comes to an end, The Undertaker’s legacy will live on as “The Phenom,” with contributions to WrestleMania celebrated and informed by fans and future generations of wrestlers. That states how big The Streak actually is and the legacy of The Undertaker’s unparalleled career as one of the greatest performers in WWE history.