The Most Shocking Upsets in Wrestling History

23 July 2025

Wrestling has always been the land of giants, legends, and larger-than-life personas. But let's not pretend it's predictable. One minute you're betting the house on a powerhouse like Brock Lesnar or The Undertaker, and the next, you're watching a rookie or underdog unseat the king of the ring like it’s just another Tuesday night. Shocking upsets aren’t just rare—they’re the adrenaline-packed curveballs that keep fans on the edge of their seats.

In this no-holds-barred breakdown, we’re diving deep into the most jaw-dropping, logic-defying upsets in wrestling history. Whether you’re a hardcore wrestling nerd or a casual fan who loves a good underdog story, buckle up—this one’s for the ages.

What Makes a Wrestling Upset Truly Shocking?

Before we jump into the chaos, let’s clear something up. Not every unexpected win counts as a real upset. We’re talking about the matches where the outcome had jaws on the floor, the kind of wins that made headlines, changed careers, or proved that anything can happen between those ropes.

The best upsets mix sheer surprise, high stakes, and a David-versus-Goliath storyline that hits you right in the feels. It’s that "no way he just pulled that off" moment that gets burned into wrestling lore.

1. The 1-2-3 Kid Beats Razor Ramon (1993)

Let’s kick things off with one of the OG shockers. In 1993, Razor Ramon was a rising star in WWE (then WWF). He had the look, the attitude, and the in-ring skills. Enter the 1-2-3 Kid—a scrawny, fresh-faced underdog with zero momentum.

People thought this was just a warm-up match for Razor. Instead, what they got was a blink-and-you-miss-it upset when the Kid pulled a moonsault outta nowhere and got the pin. The crowd? Exploded. Razor? Absolutely stunned.

This wasn’t just a win—it was a statement. Overnight, the 1-2-3 Kid became must-see TV.

2. Brock Lesnar Eats the RKO – Clean (2016)

Okay, Brock Lesnar is a monster. Period. The man broke the Undertaker’s WrestleMania streak, tossed John Cena around like a ragdoll, and basically made suplexes trendy again.

So when he faced Randy Orton at SummerSlam 2016, everyone expected another Lesnar beatdown.

But nah—what went down was insane. Orton hit a brutal RKO "outta nowhere" and left Lesnar open long enough to get his skull busted open (legitimately), leading to a technical knockout. It was raw. It was real. And it reminded everyone that even beasts bleed.

3. Rey Mysterio Wins the 2006 Royal Rumble

Now this was emotional.

Rey Mysterio—a cruiserweight, mind you—entered the Royal Rumble at #2 and lasted over 62 minutes. He outlasted monsters, legends, and everything in between, all while honoring the late, great Eddie Guerrero.

Nobody thought he’d stand a chance. And yet, by some miracle of lucha-libre heart and hustle, Rey eliminated Randy Orton and won the whole damn thing. It was a victory that—no exaggeration—shook the wrestling world to its core.

4. Jinder Mahal Becomes WWE Champion (2017)

Look, Jinder Mahal’s WWE title win still triggers people—and for good reason.

Before 2017, Mahal was booked as a jobber. He’d lost more matches than people could count. And then out of nowhere, he wins a six-pack challenge, gets a title shot, and beats Randy Orton for the WWE Championship.

This wasn’t just surprising. It was mind-blowing. WWE swerved hard and gave us something fresh, even if it left a lot of fans scratching their heads.

Was it controversial? Hell yeah. Was it shocking? You bet your boots it was.

5. Santino Marella Almost Wins the Royal Rumble (2011)

Okay, technically this isn’t an upset win—but it still deserves a spot just for how close it came to being one.

Santino Marella was the comic relief guy, not someone you expected in a Royal Rumble final two. But at the 2011 Rumble, he shocked the world by sneaking back into the ring after everyone forgot he hadn’t been eliminated. When he hit Alberto Del Rio with the Cobra and almost got the win, fans LOST IT.

Alberto survived, but make no mistake—Santino was literally milliseconds away from delivering the biggest shocker of all time.

6. Barry Horowitz Pins Skip (1995)

This one’s for the old-school fans.

Barry Horowitz was the lovable loser. The guy who clapped himself on the back even after getting pinned. But in 1995, in a match against Skip (Chris Candido), something absolutely wild happened: Barry actually won.

It wasn’t a fluke; it was a clean, satisfying surprise. Fans smiled, commentators lost it, and Horowitz’s win became the perfect “never say never” moment.

In a business that thrives on storyline swerve after swerve, this one just felt right.

7. Jeff Hardy Wins the WWE Championship (2008)

Jeff Hardy was always the daredevil. The risk-taker. The guy you'd cheer for but never expect to be The Guy.

But after years of near-misses, Hardy entered Armageddon 2008 as the underdog in a triple threat with Edge and Triple H.

What happened? He hit a Swanton Bomb, pinned Edge, and suddenly, he was WWE Champion.

The crowd? Nuclear.

Nobody expected creative to pull the trigger on Hardy. But when they did, it was one of the most feel-good swerves WWE ever delivered.

8. Zack Ryder Wins the Intercontinental Title at WrestleMania 32

This one had everyone doing a double-take.

Zack Ryder—who hadn’t been seriously pushed in forever—was a late addition to the ladder match for the Intercontinental Championship at WrestleMania 32. And somehow, someway, he climbed that ladder and grabbed the title.

It was wild. It was outta left field. And for Ryder, it was the culmination of years of fan support and hustle.

Sure, he lost it 24 hours later. But for that one moment? Ryder ruled the damn world.

9. The Undertaker’s Streak Ends (WrestleMania 30)

You knew this one was coming.

The Undertaker. 21-0 at WrestleMania. The streak was sacred. It was untouchable. Until it wasn’t.

When Brock Lesnar pinned Taker at WrestleMania 30, the world stopped. The crowd reaction said it all—shock, confusion, disbelief. This wasn’t just a match ending. It was the fall of a myth.

People still debate whether it should’ve happened. But there's no denying that this was one of the most jarring moments in wrestling history.

10. David Arquette Wins the WCW World Heavyweight Title (2000)

Now hear us out.

David Arquette—the actor—winning the WCW World Championship was never supposed to happen. Yet it did. And yeah, it was a publicity stunt, but it was also one of the most shocking, head-scratching, "what did I just watch" moments of all time.

Wrestling fans were furious, and for good reason. But in terms of pure upset value? This one tops the charts.

Why Wrestling Upsets Will Always Matter

Here’s the thing: wrestling might be scripted, but emotion? That’s real. And nothing delivers emotional highs like a shocking upset.

It’s the underdog rising. The unexpected hero winning. The narrative flipping.

These moments stick with us not because they’re planned perfectly, but because they erase the line between fiction and belief. They make us feel like anything is possible. That’s magic, folks.

Final Thoughts: Expect the Unexpected

If wrestling has taught us anything, it’s to keep your guard up. Just when you think you’ve got it all figured out, someone shocking comes and rewrites the script.

Upsets aren’t mistakes—they’re masterpieces of storytelling. And whether you love them, hate them, or still can’t believe they happened, there’s no denying they’re a vital part of wrestling’s wild, unpredictable history.

So next time you're watching a big match and thinking, "No way this guy wins"—pause. Because in the world of wrestling?

Anything. Can. Happen.