Ric Flair’s Retirement, End of the Streak and More: Most Heartbreaking Moments in WrestleMania History

Published 04/05/2021, 12:41 PM EDT

WWE WrestleMania is the biggest event in professional wrestling. Nothing gets grander than it. In the 36-year-history of the show, we’ve seen many WrestleMania moments. Some are historic moments, some are emotional, and then there are heartbreaks. Today, we check out the biggest heartbreaks in WrestleMania history.


Article continues below this ad

Booker T loses to Triple H at WrestleMania XIX


Article continues below this ad

Former WCW World Heavyweight Champion Booker T jumped ship to WWE after Vince McMahon bought WCW. Booker and HHH got into a program with each other ahead of WrestleMania XIX that saw a lot of controversial segments where Triple H belittled Booker T with racist comments.

Everyone believed Booker would take vengeance for Triple H’s actions and comments by winning the World Title at Mania. Sadly, it wasn’t to be. In one of the biggest heartbreaking moments of all time, Booker T, who had the crowd behind him like crazy, lost to Triple H, leaving fans heartbroken.

“I’m sorry, I love you” – Shawn Michaels to Ric Flair

In one of the most emotional/heartbreaking moments of all time, ‘Heartbreak Kid’ Shawn Michaels defeated Ric Flair at WrestleMania XXIV, forcing the 16-time World Champion to retire. The end of the match brought tears in every person sitting inside the Citrus Bowl and those watching at home.

Shawn Michaels prepared for a Sweet Chin Music. He had no other choice but to go for it, and he did. Michaels said, “I’m sorry, I Love You” and hit the Sweet Chin Music for the victory, ending Flair’s legendary career. HBK refrained from getting his hand raised. He left the ring for Flair to bask in his glory.

The Undertaker retires Shawn Michaels at WrestleMania XXVI

The Undertaker and Shawn Michaels collided in an epic encounter at WrestleMania 25. Michaels couldn’t end The Undertaker’s streak, but he did not give up. He challenged The Undertaker for another match at WrestleMania XXVI. Taker initially refused but accepted after HBK agreed to put his career on the line.

To nobody’s surprise, Taker and HBK put on another terrific match at the ‘Show of Shows.’ The ‘Phenom’ tried everything in his arsenal, but Michaels kept kicking out. Finally, a lifeless Michaels taunted Taker with the latter’s signature taunt. This was the last nail in the coffin as Taker delivers the Tombstone, defeating Michaels and ending his career.

End of an Era




After Shawn Michaels, Triple H took up the challenge of ending The Undertaker’s streak. The two fought in an epic No DQ match at WrestleMania XXVII, but HHH insisted the ‘Deadman’ take him on once again. A Hell in a Cell match was booked with Shawn Michaels as the special guest referee.

Triple H and Taker’s Hell in a Cell bout at WrestleMania XXVIII exceeded expectations. It had the perfect blend of in-ring action, surprising moments, as well as emotion. Taken won, and post-match all three legends stood on the stage and embraced each other, marking the ‘End of an Era.’

John Cena faces defeat at the hands of The Rock

MIAMI GARDENS, FL – APRIL 1: Dwayne ”The Rock” Johnson and John Cena in action during WrestleMania XXVIII at Sun Life Stadium on April 1, 2012 in Miami Gardens, Florida. (Photo by Ron Elkman/Sports Imagery/Getty Images)

Billed as ‘Once in a Lifetime,’ John Cena and Dwayne ‘The Rock’ Johnson met inside the ring for the first time at WrestleMania XXVIII. Everyone thought the angle that started a year earlier would culminate with the ‘Leader of the Cenation’ winning against the ‘Great One.’

To everyone’s surprise, the ‘Brahma Bull‘ defeated Cena at the ‘Show of Shows,’ in his hometown of Miami, Florida. Cena was visibly upset and sat on the ramp with disappointment. Seeing the ‘Champ’ like that definitely broke millions of hearts. However, Cena bounced back the next year, defeating The Rock to become WWE Champion.

The Streak Ends





Article continues below this ad


This is definitely the biggest heartbreak not just in WrestleMania history, but in the world of professional wrestling as a whole. Brock Lesnar defeated The Undertaker at WrestleMania XXX, leaving the entire Mercedes Superdome, WWE officials, and fans watching at home in total shock.

No one could believe Lesnar ended the Streak. Hell, even the WWE tech support guy was shocked. Lesnar’s music didn’t come on until several minutes later! Either way, it happened, and the rest is history.


Article continues below this ad

We hope we don’t see any heartbreaking moments at this year’s Mania, or do you’ll want to? Let us know in the comments below!



Ishan Chavan

770 articles

Ishan Chavan is a WWE and AEW author at EssentiallySports. Being a Journalism graduate, Ishan has over six years of experience in the Media Production Industry, having worked with Viacom 18's streaming platform, Voot. A wrestling fan since childhood, Ishan's favorite wrestlers are Daniel Bryan, AJ Styles, and Chris Jericho as he feels these three have the perfect blend of wrestling and promo skills, especially Jericho.