If there was ever one fabled story that has come from professional wrestling, it was The Undertaker’s undefeated streak at WrestleMania. It had got to a point in history where most people thought that Undertaker would never be defeated at ‘The Showcase Of The Immortals’.
At WrestleMania XXX though, the streak was broken. Brock Lesnar became the one in 21-1 and with that signalled what could potentially be the end of The Undertaker’s career.
During the years of the streak, there was over 20 years of dominance, with superstar after superstar falling to the Tombstone Piledriver. Some were up and comers hoping to make a name off The Undertaker’s back, like Randy Orton, others were legends of the sport who wanted the biggest challenge they would ever face in their career.
This list will highlight some of the least convincing challengers and will tell you why everybody thought the streak would survive that particular year.
Ric Flair – WrestleMania X8
Granted, Ric Flair is one of the biggest legends wrestling has ever seen; a two time WWE Hall Of Famer and a 16-time World Champion. But back in 2002, Ric Flair made one big mistake – he upset the Deadman.
The Undertaker had been feuding with the likes of Maven (remember him?) and The Rock in the early part of 2002. At No Way Out, The Undertaker faced The Rock but lost to him due to interference from Flair, who weeks earlier had said that every person in the locker room and every fan in the arena had lost respect for Taker.
What ensued was an onslaught of emotional and physical distress for Flair. Undertaker found David Flair and proceeded to beat down the young trainee. A couple of weeks later, David got his chance for payback when he wrestled The Undertaker on an episode of Smackdown. David was at the hands of a beatdown once again from The American Bad Ass before his father got involved.
But did anybody really think that Flair could beat Undertaker on The Grandest Stage Of Them All? It was considered highly improbable due to a number of factors. First off, The Undertaker was 9-0 at WrestleMania and Vince McMahon had just realised that he was indeed undefeated. Nobody had really taken note before the Triple H match at WrestleMania X-Seven that he had beaten everybody that stood in his way. Secondly, Flair was a considerable amount older than The Undertaker. Ric Flair was 53 at the time, whereas Taker was the same age as John Cena is now – 37. On top of those increasingly insurmountable odds, Flair hadn’t wrestled since he had become part of WWE storylines in late 2001.
The two shared one of the better matches on the X-8 card (it actually ended up being the longest match on the show), but ultimately everybody knew that Flair was never going to beat Undertaker here.
Shawn Michaels – WrestleMania XXVI
The Undertaker and Shawn Michaels had shared a rivalry that had gone back further than many in professional wrestling. While not an almost constant feud like Randy Orton and John Cena, Michaels and Undertaker were sharing the spotlight from as far back as the early 90s, and it initially came to a head back in 1997, in a feud that would lead to the first ever Hell In A Cell match. Fast forward 12 years to find Michaels vs. Undertaker for the first time at WrestleMania.
It had taken an age to get the two together at the biggest event of the year. Many thought it wouldn’t happen after Michaels famously lost his smile back in 1998 and subsequently left the company. But after he returned in 2002, it wasn’t so much if they would face each other, but when. During the naughties decade, Undertaker would cement his streak by defeating a bunch of mid-carders, some of whom will be on this list as well, but it wasn’t until late in the decade that the famous parody of Star Wars happened within the WWE.
Michaels represented the light, and Undertaker the dark side, in a match that has been heralded as probably the best match to ever to take place within the WWE. Undertaker defended the streak and took his record at WrestleMania to 17-0. Michaels carried on feuding with various other talents in 2009, but come 2010 he became obsessed with the fact that he did not beat Undertaker the year before.
Michaels challenged Undertaker to face him again at WrestleMania XXVI, but Undertaker initially declined. Michaels planned to enter the Royal Rumble so he would get to choose to fight Undertaker for the World Heavyweight Championship. That dream was cruelly cut short when Michaels was eliminated, but he had a back up plan. He interfered in the Elimination Chamber match that Undertaker was in defending his title, causing him to lose the match and the title to Chris Jericho. Michaels challenged Undertaker again and this time Undertaker accepted the match, but on one stipulation: if Michaels lost, he would have to retire.
While everybody knew an amazing main event was about to ensue, Michaels was clearly out of his depth. Nobody ever wins a match with their career on the line at WrestleMania, Ric Flair would have told him that, let alone if it’s against the Undertaker. Michaels did eventually lose and bid an emotional goodbye the next night on Raw, where Undertaker came out and tipped his hat to the fallen legend.
Kane – WrestleMania XX
These three things are what plagued Kane at the start of 2004. After he had buried his brother alive at Survivor Series 2003, he thought Undertaker would never return; he thought he had killed him once and for all. He should have known you cannot kill the deadman.
Throughout early 2004, every so often when Kane was in the ring, Undertaker’s gongs would sound and a supernatural event would occur surrounding Kane. Eventually the gauntlet was thrown down and it was to be that they would have a match at WrestleMania.
By this time though, Kane was not the dominant monster that had debuted and wreaked havoc. Kane had progressively lost his edge after he had removed his mask, and that was something the WWE did not want to have to take back. The roles had been reversed and now it was The Undertaker who was causing all the anguish to his brother.
After they had initially battled at WrestleMania XIV, in a brutal match where Taker needed three tombstone piledrivers to finish his nemesis, it was obvious that this match was going to be no contest for the Deadman. He quickly finished off his sibling and the record went to 12-0.
Mark Henry – WrestleMania 22
As you would expect with a Mark Henry match, this was thrown down into the depths of the midcard at WrestleMania 22. Competing with the likes of Edge vs. Mick Foley, a triple threat match for the World Heavyweight Championship and John Cena vs. Triple H, this was always going to be one of the more forgotten matches in the history of the streak.
Mark Henry had been featured heavily as a jobber/big guy in the late 90s and early 2000s, with his stint in the Nation of Domination, his gimmick of ‘Sexual Chocolate’ and having a baby hand with Mae Young.
Henry had returned to chase the World Heavyweight Championship, but fell short in a losing effort to Kurt Angle. Overcome with rage, he did not want anybody else to win the title so he interfered in a match between Angle and The Undertaker, causing a disqualification. The Deadman then challenged Henry to a match at WrestleMania 22 – a casket match.
The stipulation was added because in reality, this was a match that garnered such little interest. WWE already had plans for Mysterio to win the title at WrestleMania to honour the late, great Eddie Guerrero, who had passed away just a few months beforehand. This meant that neither Undertaker nor Mark Henry could feasibly be involved in the triple threat, as they would have dominated the smaller competition. They got thrown together and what followed was a less than stellar match.
Undertaker was always going to win, even when Henry performed The World’s Strongest Slam on him right next to the open casket. In a match that lasted under ten minutes, Undertaker rolled Henry into the casket and they quickly moved on to other feuds.
King Kong Bundy – WrestleMania XI
In another match against a big man at WrestleMania (he has had quite a few), Undertaker was forced to take on one of the biggest of all time in King Kong Bundy. Undertaker’s plight in this feud was that the Million Dollar Corporation had stolen the urn that gave him all his powers. To try to regain his urn, he was forced to face the behemoth Bundy.
Bundy had fame in the 1980s and even faced poster boy Hulk Hogan back at WrestleMania 2 in a steel cage match for the WWF Championship. A year later at WrestleMania III, he was featured in a six man tag match with midgets, and by the same time next year he had left the company.
However he returned in the mid 90s and joined Ted DiBiase’s Million Dollar Corporation. He wrestled sparsely during his second stint with the WWE and his biggest match was this one.
Obviously with a man of Bundy’s size, Undertaker was never going to be able to Tombstone him. In what was one of the shortest matches of the now fabled streak, Undertaker finished off Bundy with a flying lariat. Bundy would soon leave the company again, but this time he would not return.
The Big Show and A-Train – WrestleMania XIX
Big Show has had the occasional push during his WWE career and A-Train had that brief spell as Lord Tensai where he seemed to be going places with the company, but this match just had awful written all over it. The streak is held in such high regard by so many people but there has been some terrible opposition The Undertaker has taken on over the years.
The only way people would have thought that Big Show and A-Train had an advantage over The Undertaker was by sheer size and the fact it was a handicap match. One on one at WrestleMania, both of these guys would get destroyed by the Deadman.
Yet another match that finished within the ten minute mark, this one featured lower on the card than Trish Stratus’ triple threat match for the women’s championship. It even needed interference from Nathan Jones who was supposed to be Undertaker’s tag team partner to finish the match. Not Taker’s best year by a long shot.
CM Punk – WrestleMania 29
CM Punk started the psychological warfare early during his feud with The Undertaker, taking advantage of the fact that Undertaker’s ‘father’ Paul Bearer had passed away just weeks before WrestleMania 29.
He took advantage of the fact that he had his own Paul at his side as well – Paul Heyman. Heyman made sure Punk got away with all his nefarious tricks and assaults on The Undertaker and his brother Kane. Heyman even dressed up as the late Bearer in a bid to ensure Undertaker would be distracted enough so that Punk could assault him with the urn.
This did not stop what was sure to be a live slaughter in the MetLife Stadium. Punk was living on borrowed time with his warfare on The Undertaker and his own personal need to break the streak.
The match itself was competitive, and was one of the best on the show, but Undertaker’s streak had got to a point where it looked indestructible. While Punk was one of the top stars of the WWE, nobody was bigger than the streak, and Punk himself paled in comparison size wise to some of the monsters that have taken on the streak and lost. Inevitably he also fell to The Undertaker and disappeared for months after.
Brock Lesnar – WrestleMania XXX
As pointed out by John Cena in his latest feud with Lesnar, ‘The Beast Incarnate’ is a mercenary; he is somebody that works for money and doesn’t seem to care too much about anything else. Brock Lesnar is also just a part timer; why on earth would the WWE let somebody beat the streak who had so little to gain from it?
There was so much talent on the roster than could have built their career around breaking the streak. The likes of Cesaro, Roman Reigns, or Big E could have profited so much from beating The Undertaker at WrestleMania. Cesaro would not just be the one who won the Andre the Giant Memorial Battle Royal.
Instead they gave the honour to somebody who will be competing for the first time since that momentous day this Sunday at SummerSlam.
Nobody believed that Lesnar would do it because The Undertaker has beaten stronger guys at WrestleMania; he has beaten smarter guys at WrestleMania. Brock Lesnar is good, but by far and away not the best choice to bequeath this honour upon.
Alas, Lesnar did defeat The Undertaker and will forever be remembered as the one in 21-1. He has truly cemented his legacy.
Big Boss Man – WrestleMania XV
In the lead up to WrestleMania XV in 1999, Boss Man was embroiled in a feud with one of the biggest superstars in the history of the WWE: The Undertaker. Needless to say, nobody was worried about Undertaker losing in this match, especially considering that this match was one that The Undertaker had previous experience in. It wasn’t just a normal match, it was Hell In A Cell.
Undertaker had been in the first ever Hell In A Cell match and had featured in a match the year before against Mankind where he had thrown Mankind off the top of the cell, and through the top of it as well. Boss Man was facing insurmountable odds here. Nobody could see him beating the Deadman.
Boss Man seemingly had the upper hand for a few moments when Undertaker was handcuffed to the cell, but he quickly became free and pinned Boss Man after a tombstone piledriver minutes later. After the match, Undertaker called to The Brood and what followed was one of the more controversial memories in wrestling history. The Brood tied a noose and fed it through the cell, while Undertaker wrapped it around Big Boss Man’s neck. The cell then rose and Boss Man was left hanging in the air.
With that signalled the symbolic death of Boss Man’s career and the end of what was a moment of madness. Undertaker was always just leaps and bounds out of Boss Man’s league.
Triple H – WrestleMania XXVIII
First bite of the cherry saw a brutal match between Undertaker and Triple H at WrestleMania X-Seven, which saw Undertaker raise his WrestleMania record to 9-0. Second bite of the cherry saw Undertaker win but get carried out of the arena on a stretcher. That was 19-0. There are few people who have challenged Undertaker twice at WrestleMania – namely Kane and Shawn Michaels. Nobody in the history of the WWE had taken three shots at him.
With that afterthought, it was always going to be highly unlikely that Triple H was going to conquer the streak. He was an accomplished wrestler in the twilight zone of his career and would have nothing really to gain from beating The Undertaker at WrestleMania apart from having that to cement his already certain legendary status within the WWE.
Obviously it was always going to be one of the best matches on the WrestleMania XXVIII card, and it was. The match turned out to be a Hell In A Cell match and they had the special guest referee of Shawn Michaels, who is the man who had his career ended by The Undertaker, as well as being Triple H’s former tag team partner and stablemate in D-Generation X.
The odds were obviously stacked against the Undertaker, but as he always has done, he took all the punishment his opponent could throw at him, built it up into a ball and threw it right back. Undertaker devastated The Cerebral Assassin with numerous tombstone piledrivers and even took a sweet chin music into a pedigree before securing the victory.
Bottom line is that nobody had beaten Undertaker in 19 attempts, and somebody who has taken three shots was never going to get it done, no matter how much he wanted to.
Do you agree with my list? Let me know in the comments!