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THE BIGGEST UPSETS IN WWE HISTORY

By Kendall Jenkins on 2019-08-22 11:40:00

Part of the reason we love professional wrestling is that we love to be surprised. When you're watching a 'legitimate' sporting contest, you usually have a pretty good sense of who's likely to win, and who's likely to lose. There are always favorites, and there are always underdogs. The same is true in wrestling - only there's a crucial difference. Because the outcomes are predetermined, the underdog can win whenever the bookers decide it's time to give the audience a shock. It's what keeps us coming back as viewers, and it's also what's given us some of the most memorable moments in WWE history. 

The results we’re going to look at in this article are those which would (and in some cases did) result in bookmakers losing a lot of money. Quite why bookmakers allow bets to be placed on pro wrestling is something of a mystery, but the majority of them at least allow the betting public to wager money on the outcome of WrestleMania, and either take the profits or suffer the losses accordingly. No company should book nothing but shock results - that’s one of the reasons WCW fell apart so disastrously - but the occasional shock now and then keeps us all on our toes, and gives us iconic in-ring moments that last forever! 

1-2-3 Kid Gets His Name

For all the criticism than the Kliq has garnered for their backstage antics over the years, nobody can deny that their members have made stars by putting people over. Sean Waltman may already have been a junior member of the notorious backstage gang when he grabbed a surprise win over Razor Ramon on Monday Night Raw in 1993, but the crowd didn't know that, and they went crazy for the victory. The story at the time was that Ramon was an arrogant, swaggering heel who rarely lost. Squash matches were still common on WWE television at the time, and so nobody gave his opponent 'The Lightning Kid' the ghost of a chance against his famous opponent. One iconic moonsault and a three count later, Waltman had a new gimmick, and Raw had gained its 'anything can happen' atmosphere. The payoff angle further down the line, in which the two became allies with a student/teacher relationship, made it all the more worthwhile. 

Horowitz Wins!

Speaking of squash matches, Barry Horowitz knew all about them. If you watched WWE television during the early 1990s, you knew the story of a Horowitz match before the bell rang. He'd come out with his fantastic mullet, pat himself on the back of his shiny ring jacket, and be looking at the lights two minutes later. If he was lucky, his opponent might allow him to get a hip toss or a dropkick in. Horowitz was a jobber's jobber, and the crowd recognized him as such. Even before his match with Bodydonna Skip (the much-missed Chris Candido, who WWE never could figure out how to use correctly), his opponent was on the microphone mocking him for his lack of success. When Horowitz turned the tables and snagged Skip in an inside cradle for the three count, the arena popped like Hogan had just won a world title match. Sunny, at ringside, was distraught. All a disbelieving Jim Ross could do on commentary could scream 'Horowitz wins!' repeatedly. We're not sure Barry himself could process what had just happened. 

Shelton Benjamin Beats Triple H

This might not be one of the most high-profile shocks of all time, but it was one of the most stunning when it occurred. On a seemingly-normal episode of RAW in 2004, Shelton Benjamin - fresh from being one half of a mid-card tag team - beat Triple H clean in the middle of the ring. Younger fans might only know Triple H's in-ring persona as 'the guy who loses most times out at WrestleMania,' but back in 2004, Triple H never lost. If you think John Cena and Roman Reigns have lopsided win-loss records, you should go back and check out how little time Triple H spent laying on his back during the first ten years of this century. In this shocker, an argument between Chris Benoit and Ric Flair at ringside took Hunter's attention away from the match, which saw him nailed by a corner splash and a flash pin for the three-count. It should have propelled Benjamin to the big time, but for some reason didn't. Fifteen years later, WWE still has Benjamin, and still don't know how to feature him correctly. 

Bruno Sammartino’s Long Reign Ends

We realize that the majority of our readership won’t remember this, so you’re going to have to take our word for it that this was the biggest shock it’s possible to imagine in a wrestling ring. Bruno Sammartino didn’t lose. He was the eternal WWE champion, undefeated for eight years, and seemingly invulnerable. The crowds in the New York area loved him, and everyone expected the villainous Ivan Koloff to be just another Sammartino to despatch on this fateful 1971 night in Madison Square Garden. Koloff had other ideas. He targeted Bruno's 'injured ribs' with a flying knee, and brought the Sammartino era to an end. Bruno's time at the top of the business was coming to an end, and so was a period of WWE history. Nobody would ever hold the world title for such a long time again. The crowd - who largely still believed wrestling was a legitimate sport - was stunned into silence. That kind of reaction wouldn't be repeated for over forty years - which leads us to our number 1 entry. 

Brock Lesnar Ends The Streak

It’s hard to imagine anything in pro wrestling ever occurring that would be a bigger shock than Lesnar beating the Undertaker at WrestleMania 30. Undertaker was such a heavy odds-on favorite for the match that the odds on Lesnar winning were longer than the odds of taking the jackpot out of a slots casino at the first attempt. Even if you were able to jackpot a mobile slots game that quickly, you’d likely have been less stunned than the Mania crowd were when the bell rang at the end of this match. You could have repeated the trick on four or five mobile slots in a row, and you still wouldn’t have got anywhere near the amount of money bookmakers lost on this. Some people were so shocked they instantly left the arena. WrestleMania XXX was supposed to be the night that Daniel Bryan was crowned the new face of WWE - and it still sort-of was - but the crowd was still reeling from the Undertaker’s loss. A quarter of a century of total dominance at WrestleMania by the Deadman had come to a brutal end. Lesnar was a conquering monster, and Taker’s aura would never be the same again. 

 

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