10 Most Heart-Breaking WWE Moments Of The 2010s

7. Shawn's Last Ride

Roman Reigns Shield Crying
WWE.com

At WrestleMania 25, Shawn Michaels came within an inch of being the one to end The Undertaker's Streak.

Over the next year, HBK became obsessed with beating The Deadman. He got the opportunity to do so at the following year's WrestleMania, but with the caveat that, if Michaels lost, he would have to retire.

The two legends put on an amazing show, leaving everything in the ring. Despite weaving an amazing narrative, the writing was on the wall for Michaels and he eventually got put down for good following a Tombstone Piledriver.

This loss closed the book on one of the greatest careers in pro wrestling history. Whilst many had seen it coming, it was still a sad sight to see the great HBK say goodbye for the last time. Well, until the Saudi money came calling.

This moment would have ranked so much higher on this list had we been writing it two years ago. The fact that HBK came out of retirement at Crown Jewel in 2018 really tainted the impact of his loss at 'Mania XXVI.

However, in isolation, this was an incredibly emotional moment, so it deserves a mention at the very least.

Contributor
Contributor

Jacob Simmons has a great many passions, including rock music, giving acclaimed films three-and-a-half stars, watching random clips from The Simpsons on YouTube at 3am, and writing about himself in the third person.