10 Biggest Wins & Most Disappointing Losses For WWE’s Top Stars

Shawn Michaels - Biggest Win (Vs. Bret Hart, WrestleMania XII)

When Vince McMahon passionately remarked that the "boyhood dream has come true" on commentary at WrestleMania XII, he was telling the truth. Winning the WWF Title meant the world to Shawn Michaels, and that was evidenced by his teary-eyed reaction post-match.

The 60-minute Iron Man affair between Michaels and old enemy Bret Hart may have critics (and many of them), but it cannot be overstated just how much this would have meant to Shawn. Finally, he had defied his size to earn his place at the top of the pro-wrestling tree.

There'd never be another feeling like that despite countless top class matches in the years since.

Shawn Michaels - Most Disappointing Loss (Vs. The Undertaker, WrestleMania XXVI)

It's important to note straight away that The Undertaker beating Shawn Michaels at 'Mania XXVI wasn't disappointing from an in-ring perspective. In fact, it was one of the greatest bouts in WWE history.

Regardless of match quality though, this was the end of an era for Michaels, because that loss brought the curtain down on his Hall Of Fame-worthy career as a professional wrestler.

It was sad to imagine a WWE without Shawn Michaels, especially considering he had battled back from a potentially career-ending back injury to have a second run with the company which arguably topped his first. Suddenly, the knowledge that HBK wouldn't wrestle again sunk in, and it sucked.