The 15 Biggest Upsets In WWE History

Love them or hate them, upsets are great.

They can act as a change from a perceived norm, especially in the case of pro wrestling. A break from the usual is absolutely essential for an entity that deals with “lack of creativity” as a make-or-break factor in audience viewership. Now, more than ever, things in the WWE seem like they suffer from overexposure and a predictability level that is absurdly high.

However, every now and then, something happens that is beyond expectation and could drastically change the direction of a storyline or the appeal of a wrestler to the general audience. When that happens, and it catches everyone off guard, it can make for some absolutely great, compelling entertainment that everyone can, if not like, at least get behind to see what happens next.

With that said, we’ve decided to compile a short list of some of the WWE’s biggest upsets. So, take a trip down memory lane and see if any of these memorable moments ring a bell.


15 Hurricane Helms knocks off The Rock

During the late 1990s / early 2000s, the WWE had quite a stock of lovable “jobbers” and low-level mid-carders, but arguably none captured the imagination as well as Shane ‘Hurricane’ Helms.

After re-branding himself with the deluded superhero gimmick, Helms found some success with WWE’s lower-tier titles, capturing the European and Cruiserweight championships. His biggest accomplishment, however, would come when he was injected into The Rock and Stone Cold’s feud heading into WrestleMania in 2003.

Their match-up would come after Helms interrupted The Rock during a promo backstage. They continue to trade funny barbs with each other until a ‘No DQ’ match between them was set for an episode of Raw. Having Helms dead-to-rights in the middle of the ring, Rock was momentarily distracted by the entrance of Steve Austin. During that brief lapse in thought, Hurricane came from behind The Rock to score a victory via roll-up pin.

A victory he would surely never forget.

14 Rey Mysterio Jr. wins World Championship


Like Mick Foley, Chris Jericho, and Eddie Guerrero before him, Rey Mysterio Jr. was not a wrestler that should have been a big time player by WWE’s logic.

However, in 2006 with his passion at an all-time high after the passing of his dear friend Eddie Guerrero and his popularity absolutely skyrocketing, Rey Mysterio Jr. pulled off an unexpected victory against established stars Kurt Angle and Randy Orton in a “Triple Threat” match at WrestleMania 22.

An emotional victory for the little guy everywhere, no doubt, as a life-long dreamed was fulfilled.

13 1-2-3 Kid beats Razor Ramon


Before they were members of the now infamous ‘Kliq’ or ‘nWo’ together, they were Razor Ramon, the bad guy who was hot on his way to the top, and an unheralded ‘The Kid,’ the babyfaced rookie.

They met one night a few months into Raw’s early history at the Manhattan Center. At that time, Raw mostly used to showcase main event or top-tier talent ruin through the low-levels and jobbers. So, it was to an absolute shock to everyone to see the undersized Kid pull out a win on the hulking Ramon. In doing so he earned the name ‘1-2-3 Kid’ and a rise in stock that got his career off the ground.

12 From The Stands to Championship Man: Santino wins IC title


While WWE is a big international company, it’s no secret that it is still very much an American product. The shows outside of the United States, and occasionally, Canada, never really seem to be anything more than a glorified cash grab that makes no headway in story-telling.

So, on that night in 2007 that Monday Night Raw emanated from Milan, Italy, you could be forgiven for not expecting a plucky stranger that was picked out of the audience to, with the help of Bobby Lashley, defeat the mammoth Umaga for the Intercontinental Championship. Santino Marella made history that night with one of the most unique debuts the WWE Universe had ever seen.

11 Shelton Benjamin Outplays ‘The Game’

Triple H is a very unique character within the WWE’s realm. He serves as a very divisive wrestler amongst fans largely due to the perception, whether merited or not, that he is in the position that he is in due to his real-life connection to the McMahon family.

In any case, Triple H is a top-flight talent in the WWE’s greater story. He is rarely beat clean or put in a position that would be of harm to him. With that said, it makes it all the more shocking that the ‘Cerebral Assassin’ was dealt a loss to the relatively young and inexperienced newcomer Shelton Benjamin on a 2004 episode of Raw.

The loss caught everyone by surprise and is now, rightfully, heralded as one of the best upsets in WWE history.

10 Hart to Hart: Owen Knocks Off Bret


There’s always something special about the idea of sibling rivalries. Bret and Owen Hart’s feud was no exception. In fact, it was exceptionally. Looking back on it, it still holds up as some of the best storytelling that has ever taken place under the WWE banner.

The talented, but unproven, younger Hart was growing resentful of his older brother and had taken to telling anyone who would listen, just how good he really was. So, as fate would have it, the two were destined to have a match at WrestleMania X. Bret was told that in order to have his shot at the Championship title, he would first need to go head-to-head with this younger brother.

What followed was an absolutely classic wherein Owen Hart secured an unexpected victory against main-event star Bret. While Bret Hart went on to win the title later that night, it was Owen’s stand-out performance that stole the show and catapulted him into the next level on the WWE totem pole.

A must watch for anyone who has not seen it.

9 Ivan Koloff defeats Bruno Sammartino to shock the world


While many upsets would follow in WWE’s history, it’s hard to think of many bigger than when Ivan Koloff defeated Bruno Sammartino at Madison Square Garden in 1971.

Bruno Sammartino was a star. No ifs, and, or buts about it. He was the first larger-than-life champion of the people. No matter how many times he seemed down-and-out, the sold-out crowds at MSG were always there to rally him back to his feet, no matter what. He was untouchable… or so it seemed.

Having been on an 8 year defense of his then WWWF Championship, it seemed absolutely inconceivable that anyone can knock him off the throne. That was until January 18, 1971 when Ivan Koloff shocked the world by delivering a flying knee to Sammartino’s “injured” ribs and landed a pin-fall victory to absolutely stun the New York faithful.

Silence followed and the wrestling world was never the same again.


8 Maven upsets The Dead Man


WWE’s Tough Enough, for the most part, never really made the indelible mark that it hoped it would. However, it certainly did give us at least one fantastically memorable storyline that won’t soon be forgotten.

The Undertaker is a pretty untouchable guy. So much so that it caught absolutely everyone off guard when the reality show winner, Maven, eliminated him from out of nowhere in the 2002 edition of Royal Rumble. So, massive was the act that The Undertaker simply couldn’t let it be. He proceeded to remove Maven from the ring and mercilessly beat him all over the arena for the rest of the night.

This would not be the last we’d see of the two against each other as weeks later The Undertaker would defend his Hardcore Championship title against Maven on an episode of SmackDown. The Undertaker thoroughly dominated the young upstart and was about to close him out, that is until The Rock, who was feuding with ‘The Dead Man’ at the time, came out to knock him out, leading to a Maven victory that will be forever etched into the history books as one of WWE’s biggest upsets.

7 Barry Horowitz Finally Wins!

Have you ever heard Warren Zevon’s song ‘Hit Somebody!’? No? Alright, let me give you a quick rundown.

It tells the story of Buddy, a career hockey goon whose only dream was to score a goal. Now, replace hockey with wrestling, Buddy with Barry Horowitz and you have a similar tale of a down-and-out protagonist.

Barry Horowitz famously had never won a single match since his arrival to WWE in 1987. So, it wasn’t unreasonable to think that, if you were watching that July episode of WWE programming in 1995, you could go for a bathroom break and not miss anything. On this night however, you would’ve been wrong. Like, “missing a great moment in underdog history” wrong.

After being taunted by Skip of the Bodydonnas about having never won a match and being a perennial loser, Barry Horowitz, the man who had never landed that sweet 1-2-3, mustered enough to energy to get Skip into a cradle and score the legendary pin-fall victory!

6 Into the Golden Era: Iron Sheikh defeats Bob Backlund


While Bob Backlund was a fantastic champion with a distinguished career, one can’t help but think whether or not he has been overlooked when re-examining WWE’s history. Backlund’s tenure was, for what it’s worth, somewhat sandwiched between two of the greatest tenures in WWE’s history: Bruno Sammartino and Hulk Hogan.

With that being said, Backlund was a big deal and therefore it was pretty big deal when on December 26, 1983 The Iron Sheikh shocked the Madison Square Garden crowd by defeating the champion.

This loss would ultimately mark the end of Backlund’s era and help WWE usher in the “Golden Era” of professional wrestling. Suffice it to say, it was an upset loss with massive ramifications.

5 KO’d: Kevin Owens beats John Cena in main roster debut


Current Intercontinental Champion Kevin Owens has certainly taken the WWE by storm since he arrived on the scene less than one year ago.

While Owens had been a mainstay on the independent scene for quite some time, he only debuted in the “developmental” ‘NXT’ brand of WWE fairly recently. He began with authority, crushing CJ Parker and ultimately taking out best friend Sami Zayn mere minutes after he arrived. He went on to defeat Zayn for his title, and, subsequently injure him two months (to the day!) later.

It was not long after that that Owens involved himself with John Cena, as he felt Cena was taking credit for incapacitating Zayn. Owens, who hadn’t even had a match on the main roster called out Cena to a bout at 2015’s Elimination Chamber.

In an unprecedented manner, Kevin Owens, wrestling in his first main roster match, came out with a clean victory over John Cena. In doing so, Owens secured one of the biggest upsets in current-day WWE.

4 Eddie Guerrero Wins and Retains WWE Championship


Eddie Guerrero was always a great wrestler, but his legacy’s importance has only risen since his untimely passing. However, there was a time when the late, great Guerrero wasn’t as celebrated as he is now.

After recovering from a well-known bout with drug and alcohol addiction, perennially mid-carder, Eddie Guerrero set his sights on the top. However, with WWE’s booking history in mind, few expected him to have the success he had. Not many would have guessed that Eddie Guerrero would overcome the odds against “The Next Big Thing” Brock Lesnar and win the WWE Chmapionship right before WrestleMania XX or that he would also improbably retain it against Kurt Angle at the company’s marquee event shortly thereafter.

These days not many will question you on Eddie Guerrero’s abilities, but when they once did, Eddie rose to the occasion to score an upset so grand it will be remembered for all time.

3 “Mrs. Foley’s baby boy!”


In the WWE, there are wrestlers who are meant to be stars and wrestlers meant to make the stars look good. Mick Foley was, for all intents and purposes, was one of the latter.

It is arguable that for all the guys who “shouldn’t have won, but did,” that they wouldn’t have been able to make the mark that they did without Mick Foley shattering the glass ceiling before them.

On January 4, 1999, in Worcester, MA, Mick Foley’s dreams came true on Monday Night Raw as he defeated The Rock to become WWE Champion. As an added bonus upset, WCW’s Tony Shciavone famously gave away Raw’s results during Nitro (as Raw wasn’t live at the time) saying sarcastically "that'll put a lot of butts in the seats" in planning to spoil Mick Foley’s special evening. It ultimately back-fired on WCW as fans tuned in to watch Foley achieving the feat instead of Nitro’s main event; WWE won the ratings battle for the night… an additional point of pride for the ultimate underdog, no doubt.

2 Brock Lesnar Ends ‘The Streak’


Simply put, this might just be the biggest upset in WWE history.

It’s incredibly hard calling any Brock Lesnar victory an “upset,” but given the magnitude of Undertaker’s undefeated streak at WrestleMania, it’s too hard not to. The Undertaker just didn’t lose at WrestleMania! It was an established fact that was handed down for generations of fans. So, when Brock Lesnar hit that third F5 and the ref’s hand hit the mat, 1, 2, 3, no one could believe it. It gave us a fan reaction not seen since perhaps Bret Hart’s screwjob or Bruno Sammartino’s defeat to Ivan Koloff, albeit on a much, much grander scale than either of those two matches.

There’s no other way to put it: this loss marked the end of an era.

1 Undisputed Champion: Chris Jericho beats all-time greats to secure both titles

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Chris Jericho is another example of a guy who wasn’t supposed to get to the top. He was deemed undersized, and therefore, not credible as per WWE’s staus quo approach to booking top level champions. Chris Jericho took it upon himself to get his opportunity at the top, and in doing so, scored two memorable WWE Championship victories. One counted, the other one didn’t.

One could argue that Jericho’s breakthrough into top flight TV time on Raw came after his shock “victory” against Triple H on a throwaway Monday Night Raw. The crowd went wild with the upset, but, alas, it wasn’t meant to be as the ruling was overturned and Jericho was admonished back to the mid-card. However, the seed had been planted and within due time it was yet another upset victory that firmly cemented Chris Jericho as a household name.

At Vengeance in December of 2001, Jericho captured both the World Championship and the WWE Championship by beating The Rock and subsequently Steve Austin in the same night to become the first ever Undisputed World Champion. It may have taken a bit of help from outside interference, but Jericho scored the massive upset none-the-less and finally etched his place into the history books.

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