Top Wrestlemania Upsets, Ranked

"I'm going to the main event of Wrestlemania! Where're you going?" Like Randy Orton once said, you know where to find me each year come Spring—tuning in to the premiere wrestling event of the year. We're ranking the biggest upsets and surprises at Wrestlemania over the years.


The signature event on the wrestling calendar each year is Wrestlemania. While there are a lot of great events throughout the year like the Royal Rumble and Survivor Series, Wrestlemania is the Super Bowl of wrestling.

Naturally, given that it’s such a big stage with such a big audience, the powers that be of sports entertainment have helped coordinate some of the biggest surprises at these annual spectacles. We’ve gone back in time and compiled a list of some of our favorites, so read on below to take a trip down memory lane and rank the biggest upsets in Wrestlemania history.

1) The Undertaker’s Streak Is Over

Wrestlemania XXX

It’s one of the most impressive streaks in all of sports (entertainment) history: The Undertaker’s undefeated run at Wrestlemania’s. He hadn’t lost in 21 straight Wrestlemania’s and most people just assumed that would continue when he faced Brock Lesnar in New Orleans, Louisiana at the Mercedes Benz Superdome.

However, Lesnar stunned the onlookers when he hit his F5 and then pinned The Undertaker for the three-count.


Many fans obviously realized that Lesnar was qualified and good enough to win the match; the reality was that nobody thought it would actually happen. Undertaker had been winning at Wrestlemania’s for so long, it was just assumed he’d finish his career that way. Lesnar pulled quite the plot twist with the win and while it was hard to accept, reality set in after a little while.

2) Owen Hart Tops His Brother Bret

Wrestlemania X

The scene was set at Madison Square Garden. While it wasn’t the main event of the evening, in many ways it was. The opening bout at Wrestlemania X was the Owen Hart-Bret Hart brother-on-brother showdown.

Bret was the star. As a matter of fact, The Hitman had another bout later that evening as part of the main event; this was just an appetizer for him. As for Owen, he was supposed to be simple fodder. At the time, Owen didn’t really have a solidified role in wrestling as he was given many gimmicks and was even cut at one point. However, this was his “Super Bow” and he really shined.

In what was expected to be a strong effort from Owen only to lead to a Bret win, many were surprised when it was Owen who came out on top.

3) Fandango Stuns Jericho, Audience

Wrestlemania XIX

Chris Jericho is a wrestling legend and one of the things that got him so much love was his character. He was a silver-tongued devil who was slightly a bit too arrogant. Many times, it worked out in his favor at Wrestlemania 29, it cost him.

Jericho got a little too cocky when facing wrestling newcomer Fandango. The WWE was trying to build Fandango up into a star at the time and he ended up winning in cheap fashion, rolling up Jericho in an inside cradle. Everyone just assumed Jericho, the first undisputed champion, would roll out of it but when the three-count hit, the crowd felt silent.

Even Jericho was stunned. In the end, it would prove to be the biggest highlight of Fandango’s career—and one of the biggest lowlights of Jericho’s.

4) Triple H Beats “Street Thug” Booker T

Wrestlemania XIX

Wrestlemania 29 was full of surprises. This one was a stunning result and one that surely wouldn’t fly nowadays in terms of a storyline.

It’s kind of unclear why the WWE decided to go down this route but they set up a feud between Triple H and Booker T that had some serious racist undertones. Without delving too deeply into it, at one point, Triple H had called Booker T a “street thug”. It set things up where Triple H was viewed as a heel and many were cheering for Booker T to stick it to the man. It was somewhat assumed that that’s what would happen at Wrestlemania.

Instead, the heel DIDN’T get what he deserved. Booker T was beat fair and square, which made an ugly situation even uglier. Fans were somewhat appalled at the end of it as it felt really uncomfortable and surprising to see the WWE go this route.

5) Hogan Gets Pinned?!?

Wrestlemania VI

Hulk Hogan came into Wrestlemania 6 not having been pinned in about five years. Well, he did have the loss to Andre The Giant but let’s be fair: that was controversial. For all intents and purposes, he really hadn’t lost in about a half-decade.


At his Wrestlemania 6 match, Hogan was getting worked early on by the Ultimate Warrior but mounted his signature comeback – as he typically did – and many just assumed he’d pull out the win. Hogan was gaining steam with the crowd at his back, and it fell like all that was left was to drop the big leg boot on the Ultimate Warrior and that would be that. However, Warrior moved out of the way, hit the Big Splash shortly after shocked the audience when he pinned the ‘Hulkster’ for the win.

6) McMahon Helps The Family

Wrestlemania 2000

One of the biggest surprises in Wrestlemania history was the result in 2000. Keep in mind that at the time, throughout the first 15 Wrestlemanias, a good guy had always won at the end of the night. Babyfaces – the opposite of heels – had won every single time, so fans got to go home satisfied seeing either Hulk Hogan, Randy “Macho Man” Savage or “Stone Cold” Steve Austin on top at the end of the show. However, Wrestlemania 2000 broke that streak.

The main event was a matchup between Triple H and The Rock. Of course, the assumption was that The Rock would stand tall and at the end of the night, he’d be crowned champion. That was the trend; no matter what way, he’d find a way.

However, the WWE had other plans. Triple H, married to Vince McMahon’s daughter, got some help from his father-in-law. The Rock got double-crossed by McMahon and that led to Triple H getting the win and retaining his belt.

It was a stunning result because everyone was expecting to go home happy with peace of mind knowing that Triple H got stuffed. Instead, not only did The Rock lose and Triple H won, but McMahon helped the heels. It’s not what was expected, that’s for sure.

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