Back in his days at World Championship Wrestling, The Undertaker was a big, athletic, mid-card performer trying to make his way into main-event status. However it did not work out, and as he arrived to the WWE in the early 90's, he was given a character that was one of the many "over-the-top cartoon characters" that Vince McMahon preferred, but fans and people hated. Many felt that the character would not be successful later on. But as years would pass, the character went through many different changes and adaptations, which made The Undertaker more unique, mysterious, and most of all, feared by other superstars in the WWE locker room. With the success that The Undertaker has gotten through the years, his character today not only lasted for more than two decades, but he still makes an impact to fans and to the current and future superstars of WWE.
When The Undertaker first came in the WWE, not too many people would have predicted that he would start an undefeated WrestleMania streak that would last for over two decades. From the time it started back in 1991 until it was finally broken in 2014 by Brock Lesnar, The Streak was one of the reasons why The Undertaker still is one of the most popular superstars of the WWE. Today, his streak has become a big part of his career that a match with The Undertaker at WrestleMania was considered to be the same, or even as bigger as World Heavyweight or WWE Championship matches.
- The Undertaker vs Jimmy "Superfly" Snuka (1-0)
- Even though The Undertaker has defeated a wrestling legend in less than 5 minutes, this match wasn't viewed as anything special at the time. No one had a clue that this was the start of something special. With Hulk Hogan ending Sgt. Slaughter's evil grasp on the title, and the Ultimate Warrior sending Randy Savage into retirement, very few people paid much attention to this match.
- The Undertaker vs Jake "The Snake" Roberts (2-0)
- This was one of the most memorable matches from The Undertaker's WrestleMania winning streak. It was also one of the best feuds of The Undertaker's career. Jake Roberts has long been known as a master of the microphone. With The Undertaker not speaking that often at the time, Jake Roberts skillfully used his brilliance of ring psychology to bring the best of The Undertaker. He ultimately dominated the Snake almost the whole time of match. He even withstood the impact of Roberts' famous DDT after being hit by the move two times. The Undertaker won the match after performing his signature Tombstone Piledriver on Roberts to the concrete floor.
- The Undertaker vs Giant Gonzales (3-0)
- This was the only WrestleMania match in The Undertaker's career that he won via disqualification. It happened when the Giant Gonzales suffocated The Undertaker with a cloth soaked in chloroform in which his manager, Harvey Wippleman, gave him during the match. This knocked the Phenom unconscious and was brought on a stretcher to be treated backstage. After a couple of minutes, a gong sounded, and The Undertaker stormed back into the ring and attacked Gonzales for knocking him out. The Phenom hits him with three clotheslines, which the final took the giant down from his feet.
- The Undertaker vs King Kong Bundy (4-0)
- At the 1995 Royal Rumble, The Million Dollar Corporation (which included King Kong Bundy), stole The Undertaker's signature "Urn" after his match with Irwin R. Schyster. Undertaker looked for revenge at WrestleMania and defeated King Kong Bundy after a flying clothesline. He may not have retreived the urn back (because of Kama taking it back from Paul Bearer after The Undertaker claimed it from Ted DiBiase during the match), but The Undertaker have made an impact on The Million Dollar Corporation after the match.
- The Undertaker vs Diesel (5-0)
- The feud between The Undertaker and Diesel started after they interfered in each other's quest for the WWE Championship. Having nothing to gain from it, they decided to settle it at WrestleMania XII to a grudge match. It was also one of the memorable matches of The Undertaker's WrestleMania streak, where two big men fought each other into a stalemate, trading big boots, clotheslines, and finishers from each other. The Undertaker also withstood Diesel's finishing move Jacknife Powerbomb after being hit two times. After a chokeslam, The Undertaker finishes it with a Tombstone Piledriver, and the fight between two of the biggest men in the WWE was over.
- The Undertaker vs Sycho Sid (6-0)
- This was first of the three title matches in which The Undertaker competed at WrestleMania. During the main event, The Phenom entered the squred-circle with his old ring attire (trench coat, hat, gray tie, gloves, and boots) that he used during his early days. As the match started, the two trade finishers with each other, but that did not work too well. The two big men fought each other to a great match, but after two interferences from Bret Hart, The Undertaker pins Sycho Sid with a Tombstone Piledriver, thus not only improving his streak to six wins, but also claiming his second WWE Championship after six years.
- The Undertaker vs Kane (7-0)
- This was the first of the two matches against his brother Kane at WrestleMania. The feud between the two began at the 1997 Badd Blood, when Kane cost The Phenom the first ever Hell in a Cell match against Shawn Michaels. At first, The Undertaker, overcame with his emotions to his own brother, refused not to fight him. But as Kane and Paul Bearer forces him to do so week after week, he was almost being convinced, but ending up getting his emotions have the best of him, therefore still refusing to fight Kane. After being locked into a casket and setting it on fire during the 1998 Royal Rumble, The Undertaker finally agreed to fight his brother at WrestleMania XIV. During the match, The Phenom was almost dominated by Kane, because it is still against his will to fight his own brother, but after delivering three tombstone piledrivers, The Undertaker won the match even though the fight between them is not yet over.
- The Undertaker vs Big Boss Man (8-0)
- This was the first of the two Hell in a Cell matches in which The Undertaker has competed at a WrestleMania. It was also the first Hell in a Cell match at a WrestleMania. As The Undertaker's Ministry of Darkness feuded with Vince McMahon's Corporation, McMahon instructed his enforcer, The Big Boss Man to fight The Undertaker at WrestleMania in a Hell in a Cell match. Though bloodied with a baton the Boss Man has used on him, The Undertaker dominated the whole match, and got the win after a Tombstone Piledriver. After the match, the Brood (Gangrel, Edge, and Christian), came from the rafters of the arena and gave their leader a noose. The Undertaker then put it on the Big Boss Man, who was still dazed from the match. As The Brood went back up, Paul Bearer is seen controlling the Hell in a Cell, which causes it to raise up with the Big Boss Man hanging on it, sending the Corporation a message.
- The Undertaker vs Triple H (9-0)
- After Triple H cut a promo on an episode of Smackdown!, telling everyone that he had beaten all he needed to beat, The Undertaker showed up and made an exclamation that Triple H have never fought or even beaten him. This started the feud between the two superstars that culminated at WrestleMania X-Seven, as The Phenom requested the match to be done. The Undertaker and Triple H fought each other that after the referee was knocked out, the fight went all the way through the crowd. It gave The Undertaker to perform a chokeslam on Triple H on a sea of WWE fans. As the get back into the ring, they traded each other's finishers, After a Last Ride from the top rope, The Undertaker pinned Triple H despite being busted open with a sledgehammer, thus improving his streak to nine straight wins. This was considered as one of of The Undertaker's greatest WrestleMania matches. This was also the time where more people started to take notice about The Undertaker's undefeated streak.
- The Undertaker vs Ric Flair (10-0)
- The feud between The Undertaker and Ric Flair began after Flair caused him the victory at the 2002 No Way Out during The Undertaker's match with The Rock. Afterwards, The Phenom challenged Flair into a match, in which Flair refuses during a number of times. After The Undertaker attacked Ric Flair's son David, and threatened to attack his daughter, Flair finally agreed to fight The Phenom in a no-disqualification match. The Undertaker may have dominated almost the whole match, but there are times where Flair got the advantage from The Undertaker. Despite the interference from Arn Anderson and the nature of a no-disqualification match, the Undertaker defeated Ric Flair after a Tombstone Piledriver. This was the year the undefeated streak took off, as The Undertaker motioned ten fingers for his ten victories after pinning his latest opponent.
- The Undertaker vs The Big Show and A-Train (11-0)
- As The Undertaker feuded with the Big Show during the late 2002, A-Train become a part of the rivalry after he attacked The Phenom after his match with the Big Show at 2003 No Way Out. Also during the time, Nathan Jones has become The Undertaker's protege, training him for their tag-team match at WrestleMania XIX. Later on, the tag-team match became a Handicap match between The Undertaker versus the Big Show and A-Train. Although fighting alone, The Phenom still dominated the whole match, and as he went into trouble, Nathan Jones came to his aid and helped The Undertaker win the match and extend his undefeated streak to eleven wins.
- The Undertaker vs Kane (12-0)
- During the Buried Alive match between The Undertaker and Mr.McMahon at the 2003 Survivor Series, Kane attacked his brother and caused him the match, thus The Undertaker being the one buried alive. After the event, Kane held a eulogy telling everyone that The Undertaker is finally dead and is not coming back. He was wrong. During the 2004 Royal Rumble match, a gong sounded, which caused Kane to freak out and be eliminated by Booker T. This followed with a series of mind games from The Undertaker that culminated to a match with Kane at WrestleMania XX. As The Undertaker came to the ring, he returned to his "Deadman" persona (with Paul Bearer on his side). As the two brother fought each other, the newly-reborn Deadman finished his brother once and for all with a Tombstone Piledriver and improve his streak to twelve straight wins.
- The Undertaker vs Randy Orton (13-0)
- It was billed as the "Legend vs Legend Killer match" for WrestleMania 21. This was one of the few moments throughout the Undertaker's Wrestlemania winning streak where fans believed that it could come to an end. Many felt that Randy Orton would get the win to help elevate him higher into the main event, but even the interferance from his father, Cowboy Bob Orton, and his RKO finishing move wasn't enough to break the streak. The Undertaker wins the match after reversing a tombstone piledriver from Orton and performing a tombstone of his own.
- The Undertaker vs Mark Henry (14-0)
- This was billed as a casket match, the first one in WrestleMania history. Despite what one editor wrote in this space earlier, this match is noted as being one of Mark Henry's better performances as he more than held his own throughout. After the match, Undertaker sends a lightning bolt on the casket.
- This match is also the last one to feature the old-style 'coffin' style casket. Subsequent Casket Matches would use modern caskets.
- The Undertaker vs Batista (15-0)
- This was one of the Undertaker's finest matches ever. The emotions were there as he was able to win the World Heavyweight Championship from Batista. Plus, the match surprised a lot of fans in that Batista performed way better than expected.
- The Undertaker vs Edge (16-0)
- Undertaker defeated Edge for the World Heavyweight Title. It was also the first match where The Undertaker win via submission (using his then-unknown Hell's Gate submission hold). However, only about 1 month later Vickie Guererro, who at the time was dating Edge, made Undertaker vacate the title due to his dangerous submission manuever, which he won the match at WrestleMania with.
- The Undertaker vs Shawn Michaels (17-0)
- Arguably Undertaker's best WrestleMania encounter, Shawn Michaels proved to be the one of the biggest threats to Undertaker's Streak. This match recieved a 5-star rating from critics due to the length and action of the match. It was named the best match of 2009 and will be remembered for many WrestleMania's to come.
- The Undertaker vs Shawn Michaels II (18-0)
- It was billed as "The Undertaker's Streak vs Shawn Michaels Career" for WrestleMania XXVI. A rematch was made as Michaels has challenged Undertaker to a rematch at next year's Wrestlemania. However, The Undertaker refused, telling Michaels that he has nothing to prove on him anymore. After Shawn Michaels caused him to lose the World Heavyweight Championship to Chris Jericho inside the Elimination Chamber by hitting him with his signature Sweet Chin Music, The Undertaker changed his mind and accepted the rematch but only if Michaels agreed to putting his career on the line. Michaels did, and two-weeks later it was announced the match could only end by pinfall or submission. Though not reaching the height that their Wrestlemania XXV match did, the added stipulation made this match an automatic classic for any wrestling fan
- The Undertaker vs. Triple H II (19-0)
- As The Undertaker returned on the February 21st episode of Raw, Triple H also made his return as he interrupted The Phenom. The Game then laid down the challenge for WrestleMania, in which The Undertaker has accepted. As weeks progress, Triple would interfere at some random matches and would deliver his finisher, the Pedigree, on the announce table to whoever superstar (Sheamus on the first and Ted Dibiase on the second) comes out, sending a message to The Undertaker. On the week before the match, Triple H would then tell everyone why Shawn Michaels could not defeat The Phenom, and that was because of his emotions, and promised that he is different person that he could end the Deadman's winning streak. Also before the match, it was announced that it will be a "No Holds Barred" match. At WrestleMania, the Deadman would gain the momentum on the start of the match. However, Triple H dominated the whole match after he brutalized The Undertaker with chair shots to the point that he cannot go on anymore. Although badly beaten up, the Phenom got up to his feet, but ended up being hit by his own Tombstone Piledriver finisher by the Game, to which he would kick out. After delivering two pedigrees and unsuccessful pins, The Game resorted on bringing the sledgehammer, thinking that it would end the match once and for all. As he was about to use it, the Deadman somehow put him into the Hell's Gate submission hold, in which he locked on Triple H for about a minute. As the Game was about to pass out, he finally submitted after the too much pressure from The Undertaker. Despite winning the match and keeping his undefeated streak intact, The Undertaker did not walk out off the arena, but instead was carried off on a cart because of too much punishment Triple H has given him.
- The Undertaker vs. Triple H III (20-0)
- This was billed as "End Of An Era" match. During a segment between Triple H and John Laurinaitis the night after the 2012 Royal Rumble, The Undertaker made a surprise return and confronted Triple H. Feeling he has not done enough after the beating he took from the Game at the previous WrestleMania, The Phenom challenged his former opponent for another rematch at that year's WrestleMania. Triple H, feeling that ending the streak would be bad for the business, refused to take the match. As weeks progressed, it was shown that every time Triple H refuses, The Undertaker started and continuously cutting his hair. On the February 20th episode of RAW, after another refusal from Triple H, The Undertaker made a notion to his other previous WrestleMania opponent, Shawn Michaels. He accused Triple H of living on his best friend's shadow and thinks that Michaels was better than The Game. When Triple H hears about it, he become irritated and finally agreed to have the rematch, and that he would finish the streak and The Undertaker's career once and for all, but under one condition. The Undertaker must face Triple H in a Hell in a Cell match (the second Hell in a Cell match in which The Undertaker competed in at a WrestleMania). Weeks later, it was revealed that Shawn Michaels was picked as the special guest referee. During their match at WrestleMania, The Game and The Deadman picked up where they left off on their previous encounter. At first, Triple H dominated The Undertaker with chair shots just like their last match. Also, this match has full of emotions not only because of the two competitors, but also because of Michaels being the referee, contemplating to stop the match as his best friend instructed him to do because of The Undertaker looking like he cannot continue, or else The Game will "end it". After being put on Hell's Gate submission hold, Michaels hit a Sweet Chin Music to The Undertaker, which give Triple H and opportunity to also hit the pedigree. Many thought that after being hit by those two finishers, the match would end and the streak would be over, but the Deadman had the instinct enough to kick out. Afterwards, The Undertaker somehow "came back to life", and attacked Triple H with fury. The Deadman finally dominated The Game until the end of the match, leaving Triple H helpless even from Shawn Michaels. Afterwards, the Game was pinned after an emphatic Tombstone Piledriver, finally The Phenom having his revenge. He now extended his streak to perfect twenty straight wins. After the match, The Undertaker and Shawn Michaels helped carry Triple H back to the locker room and as they were standing on the stage, they hugged each other that signaled an end of an era.
- The Undertaker vs. CM Punk (21-0)
- On the start of March 4th episode of "Old School Raw", The Undertaker returned after a year-long hiatus and made everyone known that he will be competing at that year's WrestleMania. At the same night, after losing to John Cena on a number one contender's match for WWE Championship at WrestleMania, CM Punk issued a challenge and promised that he would beat The Undertaker and end his undefeated streak. However, Randy Orton, The Big Show, and Sheamus, also wants to face the Phenom, and so Vickie Guerrero announced a Fatal-4-Way match between the four competitors. At the main event, CM Punk defeated the other three superstars and has fought The Undertaker at WrestleMania 29. The streak of the Undertaker survives yet another year, by defeating CM Punk: The Undertaker locked Punk in a Hell's Gate which the latter countered with an Anaconda Vice, CM Punk tried everything he can to stop the streak (Jumping from the top rope into the table...) but it still wasn't enough. The Undertaker puts Punk through a Piledriver but Punk miraculously kicks out of the pin, The Phenom then knocks out the referee unintentionally, while held by Undertaker for a Last Ride, Punk receives the Urn from Paul Heyman in the corner, CM Punk hits the Undertaker with the Urn in the back of the head. In the end, Undertaker with a second Piledriver ended the Match to extend the streak for another year.
- The Undertaker vs. Brock Lesnar (21-1)
WrestleMania winning streak
|Jimmy Snuka||VII||1991||Won Under 5 minutes||1-0|
|Giant Gonzales||IX||1993||Won via Disqualification||3-0|
|King Kong Bundy||XI||1995||4-0|
|Sycho Sid||13||1997||For WWF Championship||6-0|
|The Big Boss Man||XV||1999||Hell in a Cell Match||8-0|
|Ric Flair||X8||2002||No Disqualification match||10-0|
|The Big Show and A-Train||XIX||2003||Handicap match||11-0|
|Mark Henry||22||2006||Casket match||14-0|
|Batista||23||2007||For World Heavyweight Championship||15-0|
|Edge||XXIV||2008||For World Heavyweight Championship||16-0|
|Shawn Michaels||XXVI||2010||"Streak vs Career" match||18-0|
|Triple H||XXVII||2011||No Holds Barred match||19-0|
|Triple H||XXVIII||2012||Hell in a Cell Match/End of an Era||20-0|
|Brock Lesnar||30||2014||"The Beast" vs "The Streak"||