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The Undertaker’s Most Iconic WrestleMania Matches

The Undertaker Shawn Michaels WrestleMania 25

In anticipation of one of the most stupendous occasions in the sporting calendar, WrestleMania 38 (April 2nd and 3rd), and The Undertaker’s induction into the WWE Hall Of Fame Class of 2022, WWE has curated some of The Undertaker’s most iconic WrestleMania moments.

The Undertaker vs Shawn Michaels (WrestleMania 25)

Widely considered to be one of the greatest matches in WrestleMania history, The Undertaker’s collision with Shawn Michaels in 2009 is without a doubt one of The Deadman’s finest moments.

With the knowledge that he had never been able to defeat the Heartbreak Kid, Taker risked The Streak against his old nemesis for the very first time.

Both men went at it with everything they could muster and it resulted in a match forever etched into the minds of wrestling fans everywhere. After several near-falls, Shawn Michaels attempted to finish The Undertaker with a moonsault, only for The Deadman to improvise and hit the Heartbreak Kid with a Tombstone for the ages.

The Undertaker vs AJ Styles (WrestleMania 36, Night One)

Despite the world dealing with a global pandemic, that didn’t stop The Undertaker and AJ Styles squaring off in what is likely to go down as a classic.

Facing off in an eerie boneyard, the added effects and background music only added to the fiercely contested affair. While The Undertaker came out victorious, AJ Styles and Taker both did their part to let fans forget about the stresses of the world, even if only for one day.

The Undertaker vs Randy Orton (WrestleMania 21)

Up-and-coming youngster Randy Orton set tongues wagging with his determination to end The Deadman’s streak, and to be honest, he came pretty close!

While they had even better matches in the future, a young Randy Orton gave it everything he had and came close to the mother of all upsets but in the end, all it needed was a Tombstone from The Undertaker to silence The Legend Killer.

The Undertaker vs Edge (WrestleMania 24)

Once Edge cashed in on his Money in the Bank victory on The Undertaker, he went on to cost The Deadman the World Heavyweight Championship at Survivor Series and win it himself at Armageddon.

Protecting an unbeaten record of his own, Edge did everything he could to put an end to The Streak by resorting to a series of underhanded tactics. The Undertaker would not be deterred and finished Edge off with a Tombstone to settle the score once and for all.

The Undertaker vs. Batista (WrestleMania 23)

Following on from his iconic victory in the Royal Rumble, The Deadman wasted no time in choosing Batista as his opponent at WrestleMania 23.

A completely fearless Batista took the fight to The Undertaker from the start and had The Phenom on the ropes at many points throughout the contest, but The Undertaker, feeding off the energy from the crowd, was able to once again overcome his challenger.

The Undertaker vs Triple H (WrestleMania 27)

Fans bristled with excitement at the prospect of The Game and The Undertaker once again, and this No Holds Barred match certainly did not disappoint.

Triple H and The Deadman brawled all over the ring, determined to destroy one another with whatever weapons they could get their hands on.

The Undertaker famously overcame three Pedigrees and even a Tombstone from The Game but needed three Tombstones of his own to finally put Triple H down in what will forever be remembered as an iconic WWE match.

The Undertaker vs Triple H (WrestleMania 28)

Despite coming out victorious, his failure to leave the ring on his own terms left The Undertaker desperate for a rematch with Triple H. The Game eventually agreed, only this time, the Heartbreak Kid Shawn Michaels would serve as special-guest referee in a Hell In a Cell spectacle for the ages.

The Game and Shawn Michaels combined with a Sweet Chin Music and a Pedigree to have WWE fans all over the world terrified that this would be the end of The Streak. The Undertaker had different ideas though and finished Triple H off with a Tombstone to complete a trilogy over a decade in the making.

The Undertaker vs Shawn Michaels (WrestleMania 26)

Off the back of their classic in WrestleMania 25, fans were desperate to see The Undertaker and Shawn Michaels square off one more time. It can be said that sequels tend to disappoint when compared to the original but that wasn’t the case here.

Shawn Michaels wasn’t able to shake off his near-miss from the previous year and was hell-bent on getting ‘Taker’s attention. The Heartbreak Kid competed with the knowledge that he may never wrestle again and it was clear for all to see, taking The Undertake to the height of his limits during the bout.

The Undertaker was not to be caught up in the sentimentality though, and once again managed to overcome the Heartbreak Kid, drawing a curtain on one of the greatest careers in the history of the WWE.

WWE’s Hall of Fame 2022 airs the night of Friday, April 1, from 3am on WWE Network (then available to watch on-demand).

Don’t miss the stupendous two-night WrestleMania, streaming LIVE from Dallas, Texas, on Saturday, April 2, and Sunday, April 3 from midnight in the UK. UK fans can catch all the action on the WWE Network and BT Sport Box Office.