10 Most Heartbreaking Major WWE Defeats

2. Bret Hart Vs. Shawn Michaels (Survivor Series 1997)

Oh come on, you knew the infamous Montreal Screwjob just had to be here. After all, no list looking at the most heartbreaking defeats in WWE history would be complete without what happened to Bret Hart at Survivor Series 1997. It'll never be forgotten, and for good reason.

Even though Bret had turned heel earlier in the year (check entry #6 for that), there was still a portion of the WWF audience that revered him as a hero. Therefore, seeing Vince McMahon scream for the bell to ring mid-match - for real - to unceremoniously end his WWF tenure left a bitter taste.

This would be Bret's final pay-per-view main event in a company he'd sacrificed so much for. It was hardly a great way to wave goodbye, and is considered one of the most shocking WWE moments ever.

Seeing Bret's disconsolate expression as the gravity of the moment began to sink in broke our hearts. Pun intended.