Every Shawn Michaels WrestleMania Match Ranked

4. Shawn Michaels vs. Triple H vs. Chris Benoit – WrestleMania XX

This is a difficult match to rank for obvious reasons. Chris Benoit’s legacy was tarnished by the horrific nature of his death and that does not go unnoticed, but this match remains one of the best in WrestleMania history.

The match was contested for the World Heavyweight Championship and was the main event of the show. Triple H and Shawn Michaels had been engaged in a rivalry that had spanned nearly two years to this point, while Benoit had won the Royal Rumble. Three premiere workers all performed to their best and produced one of the best matches in ‘Mania history that sadly is almost best left forgotten.

Benoit dumped Michaels to the outside before locking Triple H in the Crossface to win the World Heavyweight Championship.

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3. Shawn Michaels vs. The Undertaker – WrestleMania XXVI

The match that ended the career of ‘Mr. WrestleMania’. The sequel to their legendary match at WrestleMania XXV, this match lived up to the hype and sent Shawn Michaels off in style.

Michaels had become obsessed with the thought of ending Undertaker’s WrestleMania streak. So much so that he took it upon himself to cost Undertaker the World Heavyweight Championship at Elimination Chamber 2010. With Undertaker seeking revenge, the two men did battle in the main event of WrestleMania XXVI. The match was a 24-minute classic that ended with Michaels accepting his fate and slapping Undertaker, prompting a tombstone to end the match and Michaels’ career.

It was a fitting conclusion to the career of the ‘Heartbreak Kid’ and a fitting end to the Michaels vs. Undertaker rivalry.

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2. Shawn Michaels vs. Kurt Angle – WrestleMania 21

This match does not get talked about enough. One of the best in either Shawn Michaels or Kurt Angle’s careers, and one of the best WrestleMania matches ever, their clash at WrestleMania 21 was a perfect blend of styles.

Michaels surprised everyone when he attempted to outwrestle the Olympic Gold Medalist but it made for a better story in the match. Angle became frustrated and thus became more vicious as he landed an Angle Slam on the ring post. The two went back and forth for over 25 minutes before Angle finally locked in the final Ankle Lock of the match. As Angle grapevined the leg, Michaels writhed in pain. He endured for as long as he could before he was forced to finally submit.

This was a masterpiece of a match, nearly unparalleled in Michaels’ career. However, there would be one match that would top even this.

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1. Shawn Michaels vs. The Undertaker – WrestleMania XXV

Many point to this as the best WrestleMania match ever. Whether you agree or not fails to change the legacy of the first Michaels vs. Undertaker match.

In Michaels’ first attempt to end Undertaker’s WrestleMania streak, the two engaged in a tremendous battle complete with drama and danger. Undertaker did his trademarked dive over the top rope to the outside and landed virtually on his head. It was a scary moment in the match but if you are aware that he did not injure himself, the accident adds drama to the match. The drama of the streak possibly ending was through the roof in Houston that night.

In the end, Michaels failed in his attempt to end the streak. Undertaker countered his moonsault attempt into a Tombstone in an all-time great finish. The move put a cap on one of the best matches of all time and the best WrestleMania match in the career of Shawn Michaels.

What is your favorite Shawn Michaels WrestleMania match? Let us know on Twitter!

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