#2 Major disappointment: The Undertaker and Kane Vs. D-Generation X (WWE Crown Jewel 2018)
Shawn Michaels announced his retirement after losing his Career vs. Streak match against The Undertaker at WrestleMania 26, in one of the most emotional moments of all time. Michaels had entertained fans for decades, so to see his legendary career come to an end was a tough pill to swallow.
For years, Michaels did what few other Superstars did, and that was stay retired. No comeback, no return match, nothing. Rightly inducted into the WWE Hall of Fame in 2011, Michaels worked well as an ambassador for the company until his shocking return to the ring in 2018.
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After he and Triple H were attacked by the Brothers of Destruction at 2018's Super Showdown, the Showstopper came out of retirement for Crown Jewel, teaming with the Game. Unfortunately, the match would not live up to standards, as the former World Champions were noticeably slower in the ring, with the Game even suffering a pectoral tear during the match.
What had been promised as an epic encounter ended being a nasty final match for the Icon.