10 Biggest WWE WrestleMania Upsets

From The Ultimate Warrior's loss to Rick Rude at WrestleMania 5 to Chris Jericho doing the job to a debuting Fandango at WrestleMania 29, these are the 10 Biggest WWE WrestleMania Upsets In History.
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Cultaholic provides video coverage of professional wrestling - including WWE (including WWE Raw, WWE SmackDown, NXT and 205 Live), AEW, IMPACT Wrestling (formerly TNA), NJPW, ROH, and more with daily news updates, reviews, lists, highlights, predictions, reactions, podcasts and much, much more.

[@Bolbi31]

Wwe’s classic take the belt away the next night gimmick

[@1nterzept661]

Lesnar's beating the Streak, Zack Ryder's IC Title win and Seth Rollins' cashing in to win the WWE World Heavyweight Title would be my best upsets.

[@AusElixir]

And possibly most last minute bookings?

[@musc1esman]

I was at Mania 31 when Rollins cashed in. That will forever be one of my favorite mania moments just because nobody saw it coming and I was in the crowd.

[@AusElixir]

@@musc1esman I wish I could have been there. I still mark out a little when i rewatch it! I'm glad you have such an amazing memory!!

[@risingspider009]

What’s wrong with zack ryder

[@luisarguelles3020]

why rollins and ryder ?

[@GalaxyGod332]

The emotions running wild with Daniel Bryan winning the WWE and World Heavyweight title and Rey Mysterio winning the World Heavyweight title. One winning at WMXXX and WMXXII.

[@MrBda241]

#5 of Owen beating Breat was a good choice.

[@miked7212]

Bret Hart*

[@markmcfc1062]

@@miked7212 7:36

[@miked7212]

Bret*

[@lynpendry]

@@miked7212 my goodness you’re slow

[@miked7212]

@@lynpendry huh ?

[@jaylanphillips7045]

I never expected Undertaker to win his second match against Shawn Michaels. HBK looked like he could go another ten years back then so it shocked me when he did leave.

[@vampirascoffin870]

Hbk said it in 2009 after his match at wm 25 he knew he was done

[@miked7212]

I think Shawn just wanted to start spending more time with his family.

[@gst013]

You seem to be forgetting that the average wrestling retirement angle lasts about 3 months...if that weren't the case and "retirement matches" were legit, I'd agree 😅

[@Drakorre]

HBK should have won that. Imagine the bangers feud in the 2010s HBK vs Punk, Bryan, AJ

[@rickygonzalez1458]

The heart break kidd

[@JagerLange]

I just realised that I completely forgot about the "Fandango 'correcting' people pronouncing his name" thing until now.

[@pratikbajpai6208]

Lesnar beating Reigns at Mania 34 was a big upset for me, given so many reports and the predictable booking of the coronation of Roman after a year of Brock as champion.

[@robinwagner7397]

Same with Drew and Lashley

[@pratikbajpai6208]

@@robinwagner7397 yes but with Roman it was way more shocking

[@MikeD974]

I think that was brilliant same when Charlotte beat Auska I remember nodq complaining how predictable mania was gonna be then when both these matches went the way they did I thought it was smart booking because noone saw it coming

[@ChrisRyot]

The cat is now excited. You may stop stroking. The Mania content is flowing lads. Really enjoy your product :)

[@chaosdromanah8620]

Zack Ryder's win was legendary

[@develboom]

i agree

[@jetshadow5795]

Then he lost it the last night rendering the win pointless

[@vampirascoffin870]

@@jetshadow5795 lolllllll facts what a waste

[@RoyFizzle]

Who actually thought Bryan wasn’t gonna win at mania? Honestly?

[@petah3930]

honestly, they treat it like they didn’t build it up the whole year. Why else would they have him in the main event.

[@hhtptai]

Y'all did NOT have to do Miz like that 😂😭

[@logankerr8090]

LT should be next in the celebrity wing. one of the best performances from a celebrity in the squared circle. kudos to both competitors

[@vampirascoffin870]

He was good i wouldnt jump the gun with your comment saying " BEST "

[@aaronramnarain8142]

Bam Bam made him look good lol

[@vampirascoffin870]

@@aaronramnarain8142 lollll THANK YOU!!!!!!

[@nbr6116]

He was for a long time. But McAfee and Rousey are giving him a serious run for his money

[@vampirascoffin870]

@@nbr6116 true

[@tonesdad0408]

7:35 the best there is, the best there was, the best there ever will be- Breat Hart

[@miked7212]

*Bret

[@tonesdad0408]

@@miked7212 *Breat

[@LuxioV2]

@@tonesdad0408 this guy doesn’t even know about Breat or Owean Hart

[@dom_dom01447]

@@tonesdad0408 *Bread

[@liluzisquirt94]

That Jim Cornette spot was terrific

[@lordtrigon1733]

Indeed, he said he plans to live long enough to piss on Vince Russo’s grave.

[@jdust4]

Owen beat Bret AND Breat?!?!

[@miked7212]

*Bret

[@miked7212]

Breat Hart I mean Bret Hart losing to Owen Hart is one of my favorite WrestleMania moments of all time. R.I.P. Owen

[@deexith9559]

The biggest upset wasn’t that “Zack Ryder won the championship at Wrestlemania 32.” It was that he lost the title the next night, and it’s such a shame that he didn’t hold the title even for a month. He was being loved the fans and still WWE didn’t push him! I don’t know why you feel that it’s an upset 🤷🏻‍♂️

[@conradcooper2710]

Upset in a competition context doesn't mean "angry" or "sad". It means an unexpected outcome. Nobody expected Zack Ryder to win that match, but he did, making it an upset.

[@deexith9559]

@@conradcooper2710 Thanks for your explanation mate! I just misinterpreted the whole video 😅

[@tranor87]

I never realised this until now but Bret vs taker was perfect for mania 11

[@miked7212]

Good job with your spelling

[@tranor87]

@@miked7212 erm, thanks I guess

[@aaronramnarain8142]

How?

[@tranor87]

@@aaronramnarain8142 well both of them had shit matches but both could of had a masterpiece

[@HandsomeSassage]

I’m surprised Brock beating Roman at Mania 34 isn’t on here

[@thesprock5270]

Cause nobody cares

[@SHIN-A]

The Bryan thing at WM 30 was not only not an upset, but one of the most predictable mania matches (both of them) ever lol

[@MikeD974]

Yeah as soon as he beat triple h you knew how it was gonna end

[@kmversion1]

Just a reminder Fandango beat Chris Jericho at Wrestlemania

[@peggytheveteran4968]

Would u say Angle beating HBK was an upset? Or at least HBK tapping out?

[@vampirascoffin870]

He lost to the best how is that an upset?

[@lordtrigon1733]

Angle needed that win so much more than HBK at the time. He was a main eventer yet had been jobbing so much beforehand.

[@SheriffOutlaw]

Zack and Rey's mania Victories will always be my go to feel good moments for the midcard but I'm dying over that picture you used for Rocky 🤣 that reaction broke me

[@Lenoh]

> Breat Oh boy, somebody's getting a pay cut from that one lol

[@BBNefarious]

7:39 ah, my favorite Hart Family member. Breat.

[@miked7212]

*Bret

[@bryanprocaccini9753]

Fandango is the greatest of all time

[@vijaykumars3218]

I think it's the stupidest decision taken by WWE other than breaking the Streak.

[@bryanprocaccini9753]

@@vijaykumars3218 Fandango should have broken the streak.

[@vijaykumars3218]

@@bryanprocaccini9753 let's not think about it... It was a nightmare

[@Randomperson-zt3il]

@@bryanprocaccini9753 not at all

[@martinrubio6357]

Fandango winning was awesome

[@mohsinchughtai7727]

Jokes aside, *no*

[@bealgates8594]

Still mad at Vince at breaking the streak 🤦🏻‍♂️

[@rogregg29445]

Was at mania 27 I remember the people in front of us actually storming out when the Miz won via count out 😂😂🤣

[@carribob1992]

5:01 I actually put a bet on at the bookies on Fandango beating Jericho at Mania 29. Didn't collect the huge winnings of £1.25 because it didn't feel worth it.

[@victormendes7139]

Here before watching the video, I guess the number 1 pick is going to be Undertaker losing his streak

[@pannari15]

What do you mean he kicked the leg out of his leg

[@lordtrigon1733]

Owen said it in a promo like that during the build up and some fans just won’t let it go...

[@TheVictorroque]

Breat Hart gave it all vs Owen

[@miked7212]

*Bret

[@TheVictorroque]

@@miked7212 bruh. It was spelled Breat on the video 😂

[@miked7212]

@@TheVictorroque lol

[@allhell138]

“For kicking his leg out of his leg”😂 thank you for a casual call back

[@timnaw]

How is Kofi winning the title at 35 not on this list?

[@jakekoehler1]

Wrestlemania 20’s main event didn’t make the list huh? 🤔

[@JungleBunkRootsMusic2022]

That wasn't an upset. Everyone knew benoit was poised to win the belt.

[@MessianicJewJitsu]

If Jericho won that match nobody would remember that match. It seems like they were leaning into the 'Jericho is only around to put over young talent' attitude a lot of people pointed out during that time.

[@vampirascoffin870]

But didnt part aj over at wm 32 DUMB!!!

[@gregjohnson1491]

7:38 As a huge Breat Hart fan, this one shocked me when I saw it as it happened.

[@MikeD974]

I was glad triple h kept the title at wrestlemania 2000 it was getting old that the face always wins it was refreshing to see a heel win for once

[@Lfcme]

Do I hear some vintage TripleJump music in here????

[@Lucasrobe]

Fandango was booked to win the intercontinental title at payback in 2013 against champ Wade Barrett and the miz but he suffered a legitimate concussion got replaced in the match and never became champion

[@silverback9572]

It should have been Kevin Owens Vs. Sami Zayn for the Intercontinental or United States title at WrestleMania 32 Chris Jericho Vs. Dolph Ziggler for the World Heavyweight title at WrestleMania 29 Kurt Angle Vs. Rey Mysterio for the World Heavyweight title at WrestleMania 22 The Rock Vs. Triple H for the WWF title at WrestleMania 16 John Cena Vs. Wade Barrett for the WWE title at WrestleMania 27

[@cybercatgaming6052]

I always like that photo of Bret on the babyface shoulders simply cause everyone seems happy but Lex lol

[@316whatupz]

Dishonorable mention: Kurt Angle def. HBK at Wrestlemania 21

[@lordtrigon1733]

Nah, I remember thinking Angle desperately needed to win that night (morning in my country) since he’d been jobbing so much on PPV beforehand.

[@316whatupz]

@@lordtrigon1733 The build up to the match was Kurt Angle as a heel making fun of HBK and attacking Sherri

[@ArcaneAzmadi]

When you think about it, it's indicative of how bad WWE has become over the last decade that Daniel Bryan at WM31 gets a place on this list. Yes, _in story_ it's a huge upset as underdog Bryan had to overcome 3/4 of Evolution who were out to screw him, but as the intro explains, sometimes it's just the natural culmination of the obvious story. In a competently-run wrestling company, Bryan winning wouldn't be a huge shock, because it would be the OBVIOUS booking decision to make given how popular it is. But WWE has beaten its audience down so much, spitefully booked stories specifically to upset them so many times, that it was genuinely shocking that, as Adam put it, they _did_ do the right thing by having Bryan win. And that shouldn't happen. Yes, predictability isn't good, but you should still tell the story that makes sense. If Star Wars had ended with Han flying away with his money, Vader shooting Luke down during the trench run, and the Death Star destroying the Rebel base and condemning the galaxy to an eternity of terrified Imperial oppression, it would have been a surprise, but also a shit end to the movie which would never have created a franchise at all. So I guess basically what I'm saying is that WWE is the Galactic Empire, Vince McMahon is Emperor Palpatine, and HHH is Darth Vader. I think.

[@PeacefulSubmission]

TIMELESS JORTS :D

[@rogregg29445]

Lmao

[@tamzidmohsinkhan3333]

Fandango is undefeated at WM

[@chazza2378]

He lost in the first Andre the Giant memorial battle royal at Mania 30

[@peggytheveteran4968]

@@chazza2378 No he won that match

[@idkwhatimdoing8371]

@@peggytheveteran4968 Cesaro won it

[@angelus4282]

Though I concede it still counts as an upset, I fully expected Daniel Bryan to win at WrestleMania XXX. Why? Familiarity. The storyline in that PPV was essentially a remake of Chris Benoit's win in the triple threat main event of WM XX (noticeably absent from this list... odd, given that it happened during the "Reign of Terror") mixed with Goldberg's uphill climb to the WCW title on the 7/6/98 edition of Monday Nitro.

[@kevinhorn9100]

Little kid in the WWF commercial, "BREAAAAAAAAAAAAAATTTTTTTTT"!!!!!

[@miked7212]

*Bret

[@ICRockets]

I heard once that WWE didn't book Ryder's win, but rather they told the participants "you guys can decide among yourselves who wins since whoever it is will be dropping the belt the next night anyway." Any idea if this is accurate?

[@stevenwhyte5400]

Wouldn't make sense. What if they decided Miz should win? Who would he drop the title to the following night?

[@darrenhigham753]

One other piece of information for Zack ryders is that he had filmed a commercial that aired jus after that win so was a consistentcy booking

[@theSANDMAN366]

10:37, for the 10 millionth time, I still don't see The Rock's feet touching. Its cut off, thats not proof

[@thegame941]

Actually technically the first heal to win a main event at wrestlemania was yokozuna ok Hogan took the belt straight after but he was still the first heel!

[@j_delay4691]

Owen beats "Breat" huh? Is Breat yet another Hart brother? hahaha

[@ShowdeQuetzal]

Great video, congrats to all the team

[@jerransperarman9411]

good video

[@thesprock5270]

Good comment

[@emypetcu]

Man , Adam Pacitti sure hates The Miz

[@explorewithefrain7305]

You were correct about #1!

[@multiyapples]

My favorite was Zack Ryder winning the IC Title.

[@agentorange1156]

Would Wrestlemania 10 have been better if Owen beat Bret, Luger beats Yoko, Bret beats Luger in the main event??

[@jordanmccallum8132]

LT winning wasnt an upset. Even me born in 96 watching the build up years later I knew hed sadly win.

[@KingsNerdCave]

Streaks are sadly made to be broken, and business-wise someone should have done it to make a new star, but sometimes I wonder how cool it would have been for Taker to retire around 25-0 at Mania.

[@Devitron87]

The fact people still talk about the streak ending bad or good it’s great for marketing. Brock didn’t need it no. Could Seth or roman maybe have beaten him do a steel cage so the other 2 shield members cant get in ? Who knows but breaking the streak it had to end as taker was just getting to old. But should’ve been his last match.

[@MikeD974]

I remember my friend telling me Rude was winning the ic title and I thought he was nuts

[@AlpineerTrue]

I'm shocked Brock Lesnar Vs. Roman Reigns at Wrestlemania 34 wasn't on this list

[@bellalizter7451]

I would've loved if Ric Flair did a run-in on the Bryan v HHH match. Would've been overbooking but hey 4/4 evolution took a beating 😂

[@xthevortexknightx6356]

I agree and disagree with what Heyman said in regards to Lesnar breaking The Undertaker’s streak. Yes, nobody else, (except maybe Triple H at Mania 28 I think it was), could have beat the Undertaker at Mania. Should he have lost? No. I think Taker should have been allowed to retire with the streak in tact. WWE could have at least given him that, cause for all we know, he could have very well jumped ship like the rest of them, but he stayed out of respect and ran the locker room for 25+ years. He should have gone down in Wrestlemania lore as the man who was never beat, which makes people think if he is even human. It also brings up an analogy about him wrestling people who have aged like Shawn. He could have been a metaphor for death itself, and in the end, no matter if you are The Game, The Showstopper, a Superfly, a Warrior, or even a Beast, death will always prevail, and nobody can escape it.

[@esukyd2328]

There's was no way Daniel Bryan WASN'T walking out of WM30 without the championship. Still was a great ride.

[@SuperMutant2099]

Rude worked out too because wwe had him as perfect foil for warrior after winning wwf title. I can tell you being there in msg placed was shocked was Owen winning,

[@BlackGuardianofAdam]

Who doesnt remember Owen vs Breat ? Classic

[@miked7212]

*Bret

[@BlackGuardianofAdam]

@@miked7212 Yeah mate check the Video 7:38

[@miked7212]

@@BlackGuardianofAdam *Bret

[@McMahonHater]

Wait... you were surprised that LT beat Bam Bam Bigalow? Do you think LT would show up if he was going to lose?

[@BlackGuardianofAdam]

I hope Triple H vs Booker T made the list

[@principalskinner4633]

I heard a couple of days after Wrestlemania 30 and Undertaker also confirmed in an interview last year that up until 4pm that day Taker was supposed to win the match. But then Vince had a brain fart and decided to end the streak. That was the worst decision ever. It also did nothing for Brock as he didn't need it!! What a dummy Vince really is!!

[@keithcrockett7838]

VIDEO GOT WEIRD TALKIN BOUT CENA AT THE END

[@rmwing]

Skipped to the end, good stuff lads :D

[@stevenrreyes]

you forgot the hardy boyz coming back and winning at wrestlemania 33

[@yedffgd]

Who the fuck didn't think Bryan was going to win the title at 'Mania 30 by the time the show rolled around? Once the match with Triple H was made, I thought it was pretty obvious he was going over.

[@celerum]

Lesner v taker is the exception that proves the rule that wins and losses don't matter

[@rcmanization]

was mysterio's win really an upset? it was quite obvious that he would most likely win, i felt.

[@Chigen_Atomic]

Ryder instantly losing his title to Miz pissed me off then and pisses me off now. Mysterio wasn't all that surprising given Eddiesploitation, even if rumors of him not winning are to be believed.

[@floriant4336]

The Miz is the best, anyone who thinks else is just an alien pretending to be human.

[@zsteck7]

How the crap was Ryder and Hawkins win not on this list!

[@McMahonHater]

00:11:24 ...AWWWWWESOME!

[@DarrenNoFun]

"Kicked his leg out of his leg"

[@daleclark4726]

When Rick Rude wins a match it’s never a upset I don’t care who he’s wrestling

[@barelyateam]

“barely a team” makes music for wrestling fans!

[@manchaple]

The death of the streak was the 1st wrestlemania I didn't watch live. I was convinced taker was winning!! When I seen the result I think I woke my whole street up. And my kids🤷🏽‍♂️

[@conormccarthy906]

Can't believe anyone couldn't see brock beating undertaker coming

[@Thechezbailey]

Timeless jorts 👌 👌 👌 👌 👌 👌 👌 👌

[@pnepredictable]

From a non Kayfabe point of view, Lesnar beating Reigns at Mania 34 definitely belongs on this list a head of Daniel Bryan.

[@truthfulaardvark]

It’s “biggest upsets” and then says on dainel Bryan “no matter. They didn’t expect this no matter how much they WANTED IT”

[@Wooderz245]

Why do Cultaholic keep insisting that the Fatal 4 Way at Mania 2000 was because of the botched end to the Royal Rumble. A Fatal 4 Way with a McMahon in every corner was always the plan. Chris Jericho was allegedly pegged to be the fourth man instead of Foley, but Big Show was always slated to be in the match.

[@rickisgrate]

Micheal Cole vs Adam Cole with Micheal going over next year at wrestlemania

[@wavvy_is_him]

Ummm randy vs hhh vs cena for wwe championship at WMXXIV when randy retained

[@dualrosales6107]

Those are some nice breats

[@catisreckless4647]

Honestly, I've never been a real Zack Ryder fan, but I'd be an idiot if I tried to claim that he didn't have potential star power. It's truly mind-boggling that WWE didn't do anything substantial with him. Do they hate making money or something lol.

[@perist.5161]

What about the heist of the century?

[@martinrubio6357]

Daniel Bryan winning was the true underdog story

[@seanhuggan1989]

I never understood why after the botched 2000 Rumble finish, they didn't just book Rock vs Big Show for the title shot, have Rock win, and go back to business as normal.

[@trevonburtch4014]

I feel like 8 is reaching, I was pretty sure he was going to win as soon as it was announced.