The beginning of the Streak (4–0) Early into The Undertaker's career, he would defeat various
jobbers and other established stars in squash matches, leading to a match with
Jimmy "Superfly" Snuka. The match at
WrestleMania VII ended when Snuka's attempted springboard maneuver was countered as The Undertaker caught him, and he then hit the
Tombstone Piledriver before pinning Snuka. The match has been described retrospectively as "incredibly important" for a match seen at the time as a throwaway match. In mid-1991, The Undertaker aligned himself with
Jake "The Snake" Roberts in his feud with
The Ultimate Warrior. However, during an episode of ''
Saturday Night's Main Event'' in February 1992, The Undertaker turned face and defended
Randy Savage's manager and wife,
Miss Elizabeth, from Roberts's attack. Two weeks later during a "Funeral Parlor" segment, when berated by Roberts regarding whose side he was on, The Undertaker responded, "Not yours". The feud culminated in a match at
WrestleMania VIII, where, after delivering his finishing move, the
DDT, for the second time, Roberts went to the outside to attack The Undertaker's manager
Paul Bearer. The Undertaker then recovered and delivered a Tombstone Piledriver to Roberts on the floor, before rolling him inside the ring and pinning him. Wrestler
Bret Hart was critical of the finish, in particular Roberts' role, describing him as "sneaky" for receiving The Undertaker's finishing move outside the ring, preventing a clean victory for the younger wrestler. Calaway credits Roberts for providing him with advice and insight in his early career, while Roberts said he knew from the very beginning Calaway would become a superstar as The Undertaker. In late 1992 and into early 1993, The Undertaker had been feuding with
Harvey Wippleman and engaged in matches with the various wrestlers managed by Wippleman. During the
1993 Royal Rumble, Wippleman introduced
Giant Gonzáles. Gonzáles then illegally entered the
Royal Rumble match and eliminated The Undertaker. This set up a match between the two at
WrestleMania IX, in which Giant Gonzáles was disqualified when he covered The Undertaker's face with a cloth covered in
chloroform. This was the only disqualification victory in The Undertaker's streak, as all other wins were obtained by pinfall, submission, or casket. Calaway has described it as the most physically and mentally straining match he ever wrestled, and is rated as amongst the worst matches in his career. Originally, the WWF planned to have
Nailz feud with The Undertaker and would have featured a “
electric chair match” with Nailz losing and being “
electrocuted”. This storyline would be scrapped after Nailz was fired for attacking
Vince McMahon over a financial dispute. Throughout 1994, The Undertaker was sidelined through legitimate injury and missed
WrestleMania X as a consequence. The Undertaker never losing at WrestleMania was acknowledged for the first time on commentary during Undertaker's entrance in this match.
Major feuds (8–0) At the
1996 Royal Rumble, The Undertaker faced
Bret Hart for the
WWF Championship, but
Diesel cost him the match due to interference. As revenge, The Undertaker cost Diesel his WWF Championship match at
In Your House: Rage in the Cage the following month. The two settled their feud at
WrestleMania XII, which would be Diesel's final match at the annual event before leaving the company and moving to
WCW a couple of months later. In February 1997,
Shawn Michaels vacated the
WWF Championship 3 days before the
In Your House 13: Final Four event, leaving the championship to be decided at the event in a
four corners elimination match between The Undertaker,
Bret Hart,
Vader and
"Stone Cold" Steve Austin. Hart won the match and the championship, but lost it to
Sycho Sid in a match the following night on
Raw. While Hart and Austin continued their feud, The Undertaker challenged Sid for the WWF Championship at
WrestleMania 13. Hart interfered in the match at WrestleMania 13 by hitting Sid with a steel chair. The Undertaker followed up the chair shot by Hart with a Tombstone Piledriver to Sid before pinning him to claim the WWF Championship for the second time, his first reign, in five years, only to later drop the title at
SummerSlam 1997, to
Bret Hart by an accidental chair shot by special guest referee
Shawn Michaels. However, The Undertaker would return a month later and challenged Kane to a match at
WrestleMania XIV. After Kane had kicked out of two Tombstone Piledrivers (the first man ever to do so), The Undertaker delivered a third to pick up the win over his (
storyline) brother. But the rivalry leading up to WrestleMania XIV, only would later, start the ongoing war that would last only two decades from now. The match is regarded as one of the worst and most controversial Hell in a Cell matches of all time.
The American Bad-Ass years (11–0) In early 2001, The Undertaker found
Triple H's statement of having "already beaten everyone in the business" as arrogant and untrue as the two had never met in a one-on-one match before (in fact, they had met several times on RAW is WAR in 1999). Following various brawls between their respective allies, The Undertaker and
Kane held
Stephanie McMahon hostage until then-commissioner,
William Regal, gave them matches against Triple H and the
Big Show at
WrestleMania X-Seven, respectively. Following a match involving a brawl through the crowd, The Undertaker finally pinned Triple H after using the
Last Ride. This bout marked his first WrestleMania appearance under his "American Badass" biker persona. At the
No Way Out 2002 PPV, The Undertaker faced
The Rock amidst a rivalry between the two, but would lose the match when
Ric Flair interfered, sparking a feud between the two which led to a match at
WrestleMania X8. Fought under
No Disqualification rules, The Undertaker beat Flair after delivering a Tombstone Piledriver, despite interference from
Arn Anderson. After the match, The Undertaker gestured his number of WrestleMania wins. In 2020, Calaway revealed in an interview with
Stone Cold Steve Austin that he had chosen to face Flair over
Rob Van Dam after receiving the two options from
Vince McMahon, citing Flair's legendary wrestling status. Also, according to Ric Flair, he mentioned that prior to the storyline feud between the two, Triple H told him that the Undertaker wanted to wrestle him. In late-2002,
Big Show kayfabe injured The Undertaker, who would make his return at the
2003 Royal Rumble. Although The Undertaker defeated Big Show at
No Way Out,
A-Train would attack The Undertaker, while newcomer
Nathan Jones would aid The Undertaker. Just prior to their match at
WrestleMania XIX, however, Jones would be attacked by
The Full Blooded Italians on
Heat, turning the tag team match into a two-on-one handicap match instead. Jones helped The Undertaker win by delivering kicks to both Big Show and A-Train, and allowing The Undertaker to hit a Tombstone Piledriver on A-Train to get the pinfall win. This bout at WrestleMania XIX would be the final match The Undertaker would have under the "American Badass" persona.
Defending the Streak (14–0) Survivor Series 2003 marked the end of The Undertaker's Big Evil persona, when he lost a Buried Alive Match against
Vince McMahon due to interference from
Kane. Reverting to his former Deadman persona, The Undertaker would haunt Kane throughout various matches in vignettes in the build up to the match, before his eventual return at
WrestleMania XX. The Undertaker defeated Kane for the second time at WrestleMania by executing a Tombstone Piledriver. As part of his "Legend Killer" gimmick,
Randy Orton began seeking out The Undertaker, hoping to be the one to finally end the Streak at
WrestleMania 21. Orton would go as far as attacking his on-screen girlfriend,
Stacy Keibler, and WWE Legend
Jake "The Snake" Roberts turning heel in the process, before The Undertaker accepted the challenge. The finish to the match came when Randy Orton attempted to execute a Tombstone Piledriver, only for it to be reversed by The Undertaker into one of his own. Speaking to
Yahoo Sports in 2015, Orton reflected on the success of the match, saying: "We killed it. I reversed the chokeslam into the RKO, everybody bought it, he beat my ass and that was it. He picked up another win at 'Mania, and rightfully so, because I think the WrestleMania brand and Undertaker go hand in hand". This match marked the first time "The Streak" had been properly acknowledged since WrestleMania XI and 6 years later at WrestleMania X-Seven. During the start of 2006, The Undertaker began his pursuit for the
World Heavyweight Championship, held by
Kurt Angle at the time. On an episode of
SmackDown! that aired on March 3,
Mark Henry cost The Undertaker the match, as well as the World Heavyweight Championship. As a result, Undertaker then challenged Henry to a
casket match at
WrestleMania 22. The Undertaker won the match when he put Henry inside the casket. In 2019, former WWE producer
Bruce Prichard claimed that the initial plan set out by
Vince McMahon was for Henry to win the match, with The Undertaker and other producers unreceptive to the idea. Kurt Angle claimed that Undertaker wanted to wrestle with him for a "5-star match" and let Angle break the Streak, but this plan wasn't accepted by McMahon. The match was instead held at
No Way Out.
Pursuit for the World Heavyweight Championship (16–0) Having won the
2007 Royal Rumble, The Undertaker earned the opportunity to select his opponent for
WrestleMania 23. With the option to wrestle
Raw's
WWE Champion John Cena,
ECW World Champion Bobby Lashley, or
SmackDown!'s
World Heavyweight Champion Batista; The Undertaker chose Batista, thus staying on SmackDown!. The Undertaker used his signature moves Snake Eyes, Old School, and a flying clothesline early on, before executing a suicide dive to Batista, who then retaliated by performing a running powerslam through the
ECW broadcast table. Batista put The Undertaker back in the ring and attempted a pin to no avail as he kicked out. The Undertaker recovered with a Last Ride and a chokeslam, but was unable to score a pin from either move. Batista then hit a spear and his finishing move the Batista Bomb, but The Undertaker stunned everybody by kicking out. Batista tried another, but was countered and The Undertaker hit a Tombstone Piledriver to win the World Heavyweight Championship. The genesis of the feud between The Undertaker and
Edge began on the May 11, 2007, episode of
SmackDown!, which saw The Undertaker successfully defend his
World Heavyweight Championship in a draw against
Batista in a steel cage match, after which The Undertaker was attacked by a returning
Mark Henry; Edge capitalized by cashing in his
Money in the Bank briefcase to win the championship from The Undertaker. When The Undertaker returned later that year, he restarted his feud with Batista, leading to championship matches between the pair at October's
Cyber Sunday, followed by a
Hell in a Cell match at
Survivor Series in November, with Batista emerging victorious in both, the latter due to interference from a returning Edge. The trio would have a Triple Threat match at December's
Armageddon PPV for the championship, which saw Edge become champion. In February 2008, The Undertaker would prevail in the SmackDown
Elimination Chamber match at
No Way Out to become the number one contender for Edge's championship at
WrestleMania XXIV. Although The Undertaker entered the event undefeated to much acclaim, Edge had also never lost a singles match at WrestleMania. Edge described the match as "the biggest match of my career, bar none. The main event, against The Undertaker for the world championship, it doesn't get any better". The match was full of reversals by Edge, including The Undertaker's signature moves Old School, the big boot, the Last Ride, and the Tombstone Piledriver, while hitting big moves of his own such as the Impaler DDT and the Edge-o-matic. The end of the match came when, despite Edge using a camera as a weapon, and interference from
La Familia members
The Edgeheads (
Curt Hawkins and
Zack Ryder), The Undertaker performed his
Hell's Gate submission hold after being hit with Edge's finisher, the spear. Edge would submit, and for the second year in a row, The Undertaker won the World Heavyweight Championship at WrestleMania. Meanwhile, Edge later revealed in a podcast, that the original plan for the match was to be "Streak vs. Streak", as he was originally slated to win WrestleMania 23's Money in the Bank Ladder Match, but booking eventually shifted the win to Mr. Kennedy instead. Calaway's wife,
Michelle McCool, revealed in 2020 that Edge refused the opportunity to break the Streak.
Shawn Michaels challenges the Streak (18–0) After defeating
Vladimir Kozlov on the March 2, 2009, episode of
Raw,
Shawn Michaels earned the right to challenge The Undertaker at
WrestleMania 25. The feud revolved around a "good vs evil" story, with Michaels being a
born again Christian, and Undertaker a
Lucifer-type figure. During the match, The Undertaker attempted his signature suicide dive, but Michaels pulled a cameraman in the way, leaving The Undertaker to land awkwardly on his neck; the spot was said to have "added more drama and emotion to the match, and gave it an element of realism". The cameraman was portrayed by Jimmy Snuka's son
Sim Snuka, as a nod to The Undertaker's first WrestleMania match. Michaels made a comeback, and eventually hit Sweet Chin Music, but The Undertaker kicked out. Soon after, Michaels attempted a top-rope moonsault, but was caught, and The Undertaker quickly executed a second Tombstone Piledriver to finally win the match. The Undertaker initially rejected a rematch with
Shawn Michaels at
WrestleMania XXVI, saying "a rematch at this year's WrestleMania will only result in more bitter disappointment for yourself", before Michaels retaliated by saying "I'll see you at WrestleMania. Your streak, your title, your soul will be mine". At the
Elimination Chamber PPV, Michaels cost The Undertaker his
World Heavyweight Championship, coming out from under the ring and connecting with Sweet Chin Music and allowing
Chris Jericho to pin him. Towards the end, Michaels hit Sweet Chin Music on the outside, leaving The Undertaker lay on the broadcast table, before performing a top-rope moonsault, breaking the table. At the end of a 24-minute match, after kicking out of a Tombstone Piledriver, Michaels slapped The Undertaker, leading to The Undertaker executing a jumping Tombstone Piledriver on Michaels. As a result of the loss per the pre-match stipulations, Michaels retired from professional wrestling, a moment described as "the end of an era".
Final wins (21–0) In the lead-up to
WrestleMania XXVII,
Triple H vowed to do what his best friend Michaels could not: end the Streak. After a near-30 minute bout, in a match contested under No Holds Barred rules, and after The Undertaker kicked out of a Tombstone Piledriver by Triple H, The Undertaker was triumphant when he locked in the Hell's Gate on Triple H; Triple H attempted to use a sledgehammer while in the hold, but was unable to do so before tapping out. Although victorious, Calaway
legitimately could not walk out of the arena, and had to be stretchered to the back by paramedics. and
Triple H facing off before their match The Undertaker made the challenge, as he wanted to redeem himself against
Triple H from the previous year, where he had to be stretchered out of the arena. Triple H initially rejected before accepting for
WrestleMania XXVIII. Contested inside
Hell in a Cell, and refereed by
Shawn Michaels, the match, billed as the "End of an Era" began with both men brawling in and around the ring. Shortly afterwards, with the steel steps inside the ring, Triple H hit a spinebuster on The Undertaker, who then managed to lock in the Hell's Gate, which was countered when Triple H lifted him up and slammed him on the steel steps. The match was littered with weapon shots, including 16 consecutive chair shots by Triple H, followed by a sledgehammer shot to the skull, all the while The Undertaker instructed Michaels not to stop the match. When being checked on by Michaels, The Undertaker locked him in the Hell's Gate, leaving him out cold. Replacement referee
Charles Robinson ran down to the ring after The Undertaker hit a chokeslam on Triple H, but could only make a two-count, and was then on the receiving end of a chokeslam himself. Michaels recovered and hit The Undertaker with Sweet Chin Music followed by a Pedigree by Triple H, but this wasn't enough for the three count. Both men traded finishing moves for near-falls, before The Undertaker delivered his own series of chair shots for another two count. The Undertaker won shortly afterwards with a Tombstone Piledriver. It was praised as one of the greatest Hell in a Cell matches of all time, while Triple H thought it was one of his favorite matches of his career. In a controversial angle the week before
WrestleMania 29,
CM Punk's manager
Paul Heyman, dressed as, and using the mannerisms of, the recently deceased
Paul Bearer, came out to confront The Undertaker whilst flanked by The Undertaker's signature
druids. As The Undertaker attempted to assault them, Punk, in disguise as a druid, assaulted him before pouring the ashes of an
urn, purporting to be those of Bearer's, over The Undertaker. In a 2020 interview, Calaway said that he was initially conflicted about the angle, but realized that Bearer "would have loved it", with storyline brother Kane stating it was "the biggest compliment and that's the biggest tribute". Heyman has described it as intentionally offensive and controversial. Punk has spoken of his frustrations with the build of the match, saying that he was disappointed not to be presented on television as a legitimate threat to the Streak, feeling he was "just another guy". During the 22 minute match, Punk delivered a
Macho Man elbow drop from the top rope onto The Undertaker, who was lay on the Spanish broadcast table. The Undertaker survived this, and, after Punk hit The Undertaker with the urn containing the alleged ashes of Paul Bearer, he still kicked out. The Undertaker reversed Punk's attempt to use his Go To Sleep (GTS) finishing move, and hit a Tombstone Piledriver to mark the final victory in the Streak. == End of the Streak and aftermath ==