Shawn Michaels had what seemed to be the perfect retirement match at WrestleMania 26 when he lost to The Undertaker in a Streak vs. Career match.

The bout was well-received by fans and Michaels was able to stick to his retirement despite teases and dream matches being on the table. Until 2018, when the lure of one last match alongside some of his best friends was too much.

"Was I surprised Shawn came out of retirement? 100%. Every conversation I had with him was 'absolutely not.' But at the same point, you go, 'I don't want to do this, but it's with guys...we've all been down the road for 25 years. Piece of cake,'" said Triple H on The Last Ride.

Undertaker said about Shawn's decision, "I was blown away that he agreed to do it. Even talking to him about it, he had no aspirations of making a comeback. It was a one-off."

Michaels ended up joining Triple H for a tag team match against The Undertaker and Kane at WWE Crown Jewel in Saudi Arabia.

"Being out there with those guys, it was a comfortable thing. That I can do and it sounds like fun. I felt good and encouraged about doing it," said Michaels.

Unfortunately for all parties, the match itself was described by them as "bad comedy match" with Triple H suffering a torn pectoral muscle, Kane's mask coming off, Michaels not being caught on a moonsault, and more rough looking spots.

Michaels has remained out of the ring since that fateful night.

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