One of the most iconic figures in WWE history, The Undertaker made his television debut for the company on November 22, 1990, appearing on Survivor Series as Ted DiBiase’s mystery partner, eliminating Koko B. Ware and Dusty Rhodes within minutes. That was just the beginning of a three-decade journey for the Deadman, who, more than his seven world titles, made history for an undefeated streak of 21-0 at WrestleMania until the 30th edition with his first WrestleMania career loss to Brock Lesnar. He would join a unique list of wrestlers who wrestled in the ’80s, ’90s, ’00s, ’10s, and ’20s without much interruption.
At the same time, it was also closely linked to the introduction of matches such as the Hell in a Cell, the Buried Alive match, the Casket Match and the Last Ride match and featured four times in the best match of the year for Pro Wrestling Illustrated. Here are 10 of the many, many matches of his career.
Bad Blood: In Your House (1997)
Hell in a Cell match to determine the #1 contender for the WWF World Heavyweight Championship at Survivor Series 1997
Shawn Michaels vs. The Undertaker
The first Hell in a Cell match in history. About two months earlier at SummerSlam, Shawn Michaels was designated as a referee in a match between The Undertaker and Bret Hart for the WWF World Heavyweight Championship and ended up deliberately interfering to cost the Deadman the loss.
As a result, HBK and Undertaker faced off at In Your House: Ground Zero, but the match ended in a no-contest after both attacked the referees.
It was planned that the next confrontation between the two would be in a Steel Cage match, however, a covered and larger structure was built to receive the combat.
At the same time, former The Undertaker manager Paul Bearer, who was burned in the face by a fireball thrown by the Deadman in In Your House 14: Revenge of the ‘Taker, compared this incident to what burned down the funeral home that consequently killed The Undertaker’s parents and possibly his younger half-brother. Bearer blamed Undertaker for his parents’ deaths and said he had proof that his half-brother Kane was alive and was going to the WWF to challenge the Deadman.
King of the Ring 1998
Hell in a Cell: Mankind vs. The Undertaker
In the previous pay-per-view, Steve Austin defeated Mick Foley’s alter ego, Dude Love, after interference from The Undertaker, in a difficult match refereed by Vince McMahon. The WWF Championship was at stake.
The next day on Raw is War, Kane beat The Undertaker to become the new main contender, and a week later, Kane, Mankind (another Foley alter ego), and The Undertaker attacked Austin and placed him inside a coffin.
On the June 15 episode of Raw is War, Mankind and Kane teamed up against Stone Cold Steve Austin and The Undertaker in the second Hell in a Cell match in history. The feud ended in a no-contest, after the Deadman allied Paul Bearer (then allied with Mankind and Kane) inside the cell, while Austin attacked Kane at the top of the structure.
All this led to the marking of the third Hell in a Cell in history, 13 days later, at the King of the Ring pay-per-view, with Mankind and The Undertaker. It’s fair to say that the match became rather famous…
Vengeance 2002
Triple threat match for the WWE Undisputed Championship:
The Undertaker (c) vs. The Rock vs. Kurt Angle
At the previous King Of The Ring pay-per-view, Undertaker retained the title by defeating Triple H. However, the match was marred by interference from The Rock, who at one point planted the Deadman on the mat with a Rock Bottom.
Furious at this interference, Undertaker asked Vince McMahon for a match with The Rock and the WWE owner complied, scheduling a duel between the two for Vengeance.
However, on the July 4th episode of Smackdown! , Undertaker and Kurt Angle tied in a match over the WWE Undisputed Championship, as the Deadman completed a settlement on Angle at the same time he folded.
Four days later, on Monday Night Raw, Vince McMahon announced that Kurt Angle would be added to the match on Vengeance, making it a triple threat match. And in the shows that followed up to the PPV, both Undertaker and Angle and The Rock took every opportunity to attack each other.
SmackDown! (04.09.2003)
WWE Championship: Kurt Angle (c) vs. The Undertaker
About ten days earlier at SummerSlam, The Undertaker defeated A-Train, while Kurt Angle retained the WWE Championship by beating Brock Lesnar via submission.
On Smackdown! that followed, The Undertaker demanded a title shot and eventually won it by defeating Brock Lesnar and Big Show in a triple threat match in the show’s main event.
SummerSlam 2008
Hell in a Cell match: The Undertaker vs. edge
The Undertaker and Edge had met four times in PPV for the World Heavyweight Championship over that year. In the first, at WrestleMania XXIV, Deadman won the title after securing the title shot in an Elimination Chamber PPV No Way Out.
In the second, at Backlash, Undertaker successfully defended the belt by making Edge give up with a suffocating submission, the Gogoplata. However, then-SmackDown General Manager and then-fiancée of Edge, Vickie Guerrero, stripped Undertaker of the title and banned Gogoplata to “protect the SmackDown stars “.
The two clashed again for the vacant title at Judgment Day and Undertaker won again, but by count-out, which led Vickie to argue that WWE rules did not allow anyone to win a title by count-out or disqualification. The decision was then postponed to One Night Stand on June 1st in a TLC match, a stipulation that Edge has always felt very comfortable with. Plus, if Undertaker lost, he would have to leave WWE. And Undertaker did lose, thanks to the interference of Curt Hawkins, Zack Ryder, Chavo Guerrero and Bam Neely, all members of La Familia.
Edge ended up losing the title to CM Punk, who moved to Raw but turned needles to Triple H’s WWE Championship. And it was precisely The Game that ruined the Canadian’s marriage to Vickie, by revealing a secret romance between Edge and the woman who was preparing for his marriage, Alicia Fox. Interference by the two women cost the Rated-R Superstar the loss in a title match at The Great American Bash, but Vickie announced an even heavier punishment for Edge: the readmission of Undertaker, against whom he would have to fight in the Hell in a Cell match at SummerSlam.
WrestleMania XXV: Shawn Michaels vs. The Undertaker
At a time when The Undertaker’s WrestleMania streak was at 16-0, trying to finish it was an exciting challenge for every wrestler in WWE. Shawn Michaels, JBL and Vladimir Kozlov submitted their candidacy. On the February 16 edition of Monday Night Raw, Michaels beat JBL, beating Kozlov two weeks later to secure the opportunity.
On the March 9 episode of Raw, The Undertaker and Michaels defeated Kozlov and JBL, but after the match, HBK attacked the Deadman and kick-started the mind games that took place between the two in the weeks that followed.
WrestleMania XXVI: No Disqualification Streak vs. Career match:
Shawn Michaels vs. The Undertaker
After failing to break The Undertaker’s streak at WrestleMania in 2009, in a match that won the Slammy Award for Match of the Year, Shawn Michaels challenged the Deadman to a rematch. The Undertaker, then world champion, declined.
At Elimination Chamber, Michaels interfered in the World Heavyweight Championship match, performed a Sweet Chin Music on The Undertaker, and allowed Chris Jericho to defeat him and claim the belt.
The following night, The Undertaker was shown to have changed his mind and accepted the challenge, but with the stipulation that HBK would have to retire if he lost. Shawn Michaels accepted and stressed that if he couldn’t break the streak, there would be no reason for his career to continue. Two weeks later, Michaels and Undertaker agreed to add another stipulation: the match would be without disqualifications.
WrestleMania XXVII: No Holds Barred match:
The Undertaker vs. Triple H
After several weeks of a teaser released by WWE aimed at the date February 21, 2011, that day’s episode of Monday Night Raw was marked by the return of Undertaker, who had not appeared for four months.
However, the Deadman was interrupted by Triple H, also returning. The two legendary fighters looked into each other’s eyes and then turned their faces towards the WrestleMania XXVII logo, suggesting a possible match between them in the biggest event of the year, something that came to be confirmed a few days later.
Before the second match between Undertaker and Triple H at a WrestleMania – the first was at the 17th edition – the two veterans once again faced face on the last Raw before the PPV, on March 28th. Shawn Michaels interrupted them and criticized The Game for believing he would be able to defeat Undertaker in the big event, something HBK was unable to do. After the Deadman said that Michaels was history, Michaels tried to Superkick him, but the Phenom retaliated with a Chokeslam that was stopped by Triple H. Still, Michaels once again showed disbelief about a possible victory of his fellow faction in the DX.
WrestleMania XXVIII
Hell in a Cell – Shawn Michaels as guest referee:
The Undertaker vs. Triple H
A year earlier, The Undertaker defeated Triple H via submission in a No Holds Barred match at WrestleMania XXVII. Still, for the first time in his career, he had to be taken out of the ring on a stretcher and with the help of medical staff.
After ten months without making any appearances, the Deadman made his return on the January 30, 2012 edition of Monday Night Raw, confronting and challenging Triple H to a rematch at WrestleMania XXVIII, because he didn’t want his stretcher exit to stay. like your last image.
After Triple H declined the challenge on the following week’s Raw, Shawn Michaels appeared on the February 13 episode to urge him to accept. The Undertaker returned to the charge a week later, referring to The Game as a coward, comparing his acting and career to that of Michaels. Enraged by these comments, Triple H eventually accepted the challenge and proposed that the match be a Hell in a Cell match. However, HBK announced that he would be the referee.
WrestleMania 29: The Undertaker vs. CM Punk
On the March 4, 2013, episode of Monday Night Raw, which was themed around “Old School Raw”, The Undertaker returned to WWE programming and issued an open challenge to all wrestlers to try to defeat him for the first time at WrestleMania.
CM Punk, Randy Orton, Big Show and Sheamus declared that they wanted to face the Deadman, which led to then-Raw supervisor Vickie Guerrero to arrange a match between the four of them that same night, in which CM Punk emerged victorious.
The following night, Undertaker and Kane’s former manager, Paul Bearer, died of respiratory problems.
A week later on Raw, CM Punk interrupted a Bearer tribute segment to stress that it would break Undertaker’s streak at WrestleMania. Kane didn’t like it and tried to attack Punk, but Punk managed to get away. That same night, Kane defeated Punk in a no disqualification match and then honoured Bearer along with Undertaker, but Punk interrupted them once more by hitting Kane with the Deadman’s urn. Undertaker chased Punk, but Punk got away with the urn.
On the March 18 edition of Raw, Undertaker went to the ring to say that Punk had an opportunity to return the urn to him, but Punk only appeared on the giant screen, promising that he would break the streak while nonchalantly tossing the urn into the air.
Two weeks later, Punk, who was disguised as a druid, attacked Deadman and hit him with the urn, opening it later and dumping what was in it on Undertaker, further heating the rivalry between the two…