1. Shawn Michaels Vs. The Undertaker (WrestleMania 26)
The greatest WWE retirement match of all time is, without a doubt, the clash between Shawn Michaels and The Undertaker at WrestleMania 26.
After failing to defeat Undertaker at WrestleMania 25, the Heartbreak Kid became obsessed with the idea of ending the Deadman’s legendary WrestleMania streak. After numerous failed attempts to secure a rematch, Michaels finally got his wish, but with his career on the line.
The match was contested under No Disqualification rules and served as the night’s main event. The two legends delivered yet another classic, with amazing storytelling.
The bout featured several memorable moments and near falls, and for the first time, fans genuinely believed the streak might end. But despite giving absolutely everything he had, Michaels came up short, bringing his storied career to an end.
It was an extremely emotional moment, watching Mr. WrestleMania bow out at WrestleMania itself, especially after such a breathtaking performance. Shawn would stay retired for over eight years before returning for a tag team match at Crown Jewel 2018, teaming with his best friend Triple H against Undertaker and Kane.
The match was a massive disappointment, and Shawn’s decision to come out of retirement was widely criticized. However, we can excuse it just as a one-off, and it doesn’t damage the legacy of the iconic WrestleMania match.
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