The Undertaker's 5 Greatest WrestleMania Matches

For millennials who have grown up following WWE, there is, possibly, no greater figure of reverence than The Undertaker. No other wrestler possesses the great combination of strength, athletic ability, grandness of character and commanding presence as much as The Deadman. Every year, when the biggest event of WWE, and by extension, professional wrestling calendar – WrestleMania – comes around, the name of Undertaker is bound to occupy the minds of WWE fans.

After all, the man who owns the most splendid record at this annual showpiece is none other than The Phenom. However, it seems increasingly likely that last year’s squash match that Undertaker had with John Cena would be his last ever at WrestleMania. It is clear that The Deadman is almost done with his career. His wrestling prowess has declined steeply in the last couple of years and he is now not expected to compete in a long match.

So, as sad as it is, we will now have to be content with watching videos of Undertaker’s matches from the past. This is a moment that every fan dreads but has to face. All we are left with are the innumerable memories of this legend’s career and the great moments he produced. With that spirit of recollection, let us look back at the five best matches which this icon of WWE competed in at WrestleMania – an event that he made his own.

A man, or should I say, deadman, who holds the incredible 24-2 record at the industry’s biggest annual show is bound to have had many great matches and it is very hard to select just five of them. But there have been some which surpassed others in terms of the quality of action and performance by Undertaker and his opponents. Here is a list of the 5 matches which deserve to be counted as the best in the legendary WrestleMania history of The Phenom.

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#5 The Undertaker vs Randy Orton - WrestleMania 21 (2005)

Undertaker's victory over Randy Orton at WrestleMania 21 was a key moment in WWE history

In the history of Undertaker’s famous streak, this match is a major turning point. This was the first time that the streak and its defence became the primary focus of The Deadman’s WrestleMania appearance. Randy Orton, at that stage of his career, had already established himself as a leading name and had also claimed his maiden World Heavyweight Championship a few months back. He was also being portrayed as the ‘legend killer’ due to his numerous encounters with greats of the industry and the victories he gained over them.

The story of this match started when Orton decided to challenge The Undertaker to a WrestleMania match with the intention of breaking his streak. He was a face then and the proposal of the match was made respectfully. Then, the WWE decided to cause a heel turn for him by making Orton deliver an RKO to his storyline girlfriend Stacy Kiebler – to send a message to The Undertaker. Hence, Orton entered the match as a conceited man certain to break the streak.

The match was a topsy-turvy affair keeping the fans on the edge of their seats. It ended in dramatic fashion with Orton, frustrated at not having put away his opponent after having tried all his tricks, trying to use Undertaker’s very own Tombstone Piledriver against him. The Phenom turned the move around and delivered his finisher on Orton to end the match as well as keep his streak alive.

It has been subsequently revealed that the plan was for the ‘legend killer’ to win the contest and end the streak, but the wrestler refused to play that part out of respect for The Undertaker. Thank goodness for that! Otherwise, the streak – one of the biggest attractions of WrestleMania – would have ended even before reaching the peak of its importance.

#4 The Undertaker vs Triple H: Hell in a Cell Match - WrestleMania 28 (2012)

The Hell in a Cell match at WrestleMania 28 was pulsating and dramatic

This was a rematch from the previous edition of WrestleMania. The entire contest and the storyline leading up to it was full of engrossing drama. It started when Undertaker made a sudden appearance a few weeks before WrestleMania and with his signature decapitation gesture, demanded a rematch with Triple H at that event. The Deadman didn’t want him leaving the arena after his WrestleMania 27 match to be his last image from the biggest wrestling extravaganza.

Triple H repeatedly refused to accept the challenge. There were some terrific promos featuring Shawn Michaels and Undertaker trying to provoke and convince HHH to accept the match. Eventually, during one of these promos, The Deadman tauntingly said that the real reason for The Game’s refusal was his realisation that he can’t do what his ‘buddy’ Shawn Michaels couldn’t. This, Taker said, is because he knows that HBK is better than him.

This caused HHH to come back to the ring and accept the challenge while declaring that the match will be inside Hell in a Cell. The story was complicated even more with Shawn Michaels being made the special guest referee. The match was equally dramatic. Triple H, at one stage, took out the sledgehammer and was going to smash Undertaker’s head but Shawn stopped him. Undertaker then locked Michaels into his ‘hell’s gate’ hold and HHH relieved him by hitting the aggressor with the hammer.

With Michaels temporarily down due to Taker’s assault, the latter locked the hell’s gate on Triple H and looked set to win but with the special guest referee out of action, it amounted to nothing. Then, in a heart-stopping moment, Michaels delivered the ‘Sweet Chin Music’ and Triple H followed it up with a Pedigree. Undertaker’s opponent immediately covered him and he kicked out with a microscopic second left in the three count by Michaels.

The climax was brilliant. Undertaker regained the upper hand and told HHH to stay down. But he defiantly made the DX chop to which Undertaker responded by knocking him down with Triple H’s own sledgehammer. Then, he delivered the Tombstone Piledriver and finished the match with Michaels making the three count fairly.

#3 The Undertaker vs CM Punk - WrestleMania 29 (2013)

Undertaker and CM Punk put together a brilliant match at WrestleMania 29

CM Punk was one of the most talented wrestlers in WWE. A match between him and The Undertaker was bound to be a good one. The fact that, at that time, Punk was being managed by Paul Heyman added dramatic value to the encounter.

WWE engrafted the real death of Undertaker’s famous manager Paul Bearer onto the storyline. Punk interrupted the Deadman while he was paying his tributes to the deceased man and, after attacking him, stole the famous urn which signified Undertaker’s relationship with Bearer.

The match saw brilliant action with both wrestlers building up the narrative beautifully. CM Punk performed Undertaker’s iconic ‘old school’ manoeuvre against the very man to whom it belonged. There was another great moment when Punk locked in his submission hold – Anaconda Vice – but Undertaker sat up looking fiercely at his opponent.

The collection of moves and counter-moves along with the fluctuation of advantage in the match made it engrossing. Eventually, Taker triumphed and walked away, not just with the victory, but also his famous urn.

#2 The Undertaker vs Triple H: No Holds Barred Match - WrestleMania 27 (2011)

The 'no holds barred' match between Undertaker and Triple H was one of the most intense

When Undertaker made his comeback to WWE after missing in action for some time – few weeks before WrestleMania 27 – he was interrupted before speaking even a word by Triple H. The latter looked at the mania sign hanging overhead and turned his gaze back to The Deadman.

Even without a word being uttered – by the two wrestlers or even the commentators – the match was announced. Since both competitors were veterans by then and still very much in great physical condition, the match was guaranteed to be entertaining.

And it was a pulsating contest. Both wrestlers threw everything they had at each other. There was not just a full array of moves from both competitors but also repeated use of their finishers. But neither man was willing to give up.

Triple H went to the extent of delivering Undertaker’s very own Tombstone Piledriver against him. But even that didn’t seal the deal. Then came the finish to the match which was even more thrilling.

Just when The Deadman seemed exhausted, Triple H grabbed his sledgehammer but Undertaker locked in the hell’s gate. The Game kept fighting to get out of it for a long time. But eventually, he tapped out and Taker kept his streak going.

Undertaker had to be stretchered out and on the following night on Raw, Triple H mentioned the fact while respectfully talking about his opponent. The story was continued into next WrestleMania when The Phenom demanded a rematch so that the sight of him unable to leave the stage on his feet won’t be his last WrestleMania image.

#1 The Undertaker vs Shawn Michaels - WrestleMania 25 (2009)

Undertaker vs HBK at WrestleMania 25 is widely regarded as one of greatest wrestling matches ever

There, probably, has been no greater in-ring performer than the Heart Break Kid Shawn Michaels in WWE. Due to his great exploits at the company’s biggest annual extravaganza, he earned the epithet of Mr. WrestleMania.

So, when Mr. WrestleMania took on the most successful superstar of this event – The Undertaker – it was bound to be a match for the ages. And it turned out to be just that, and more! The two legends, probably the greatest wrestlers in WWE’s history, produced a match that is regarded the greatest ever in this field by many fans and experts.

The two men crafted a contest that had everything. Both of them showed their physical prowess and athletic abilities to the fullest and developed the narrative of the match beautifully. There were several great moments including one where both wrestlers, after lying flat out in the ring, rose suddenly in their trademark style at the same time - Undertaker sitting up and Michaels doing his nip-up.

The action kept viewers on the edge of their seats. It saw both wrestlers delivering blow after blow and exhaust every weapon in their arsenal. After a duration of more than half-an-hour, the contest ended with Undertaker keeping his streak alive.

So great was the match that even The Deadman was forced to do something which went against his on-screen character – acknowledging his opponent after the win. A rematch took place the next year which proved to be the final one of HBK’s career – at least until he reunited with Triple H to face Undertaker and Kane at Crown Jewel in Saudi Arabia last year.