Ranking the Most Shocking Upsets in WWE History Ahead of Roman Reigns vs. Logan Paul

Roman Reigns will enter Riyadh, Saudi Arabia Saturday as the Undisputed WWE Universal champion, making yet another defense of the top prize in professional wrestling, this time against a social media celebrity with only two wrestling matches to his name.

Logan Paul challenges The Tribal Chief in a match that, on paper, skews heavily in the champ's favor. What if, though, he accomplishes the unfathomable and dethrones The Head of the Table?

It would rank among the greatest upsets in WWE history.

What are those upsets, though?

Take a look at this countdown, featuring the most unthinkable victories, ahead of the colossal collision and, potentially, the most historic and memorable of them all.

Fans in Milan, Italy were caught off-guard on the

Fans in Milan, Italy for the April 16, 2007 episode of WWE Raw had no reason to think the seemingly unconquerable Umaga would lose the Intercontinental Championship, much less to a fan lucky enough to sit in the front row for the night’s event.

Yet, that is exactly what happened.

Santino Marella, billed from the show’s host city, emerged from the audience to knock off The Samoan Bulldozer and win the title in a massive upset, thanks in large part to the involvement of ECW champion Bobby Lashley.

Primarily utilized as a means to continue the babyface’s rivalry with Umaga and the McMahon family, the segment launched Marella into stardom. He would go on to win that title a second time just over a year later before becoming one of the more entertaining comedy acts in WWE history.

Not bad for a fan who got lucky and scored a most improbable win.

By 1995, longtime WWE fans knew Barry Horowitz as a career enhancement talent. He was always around, on television and house shows against top stars, but always the guy tasked with making them look good.

There was no reason to believe that his match with relative newcomer, Bodydonna Skip, on the July 9 episode of Wrestling Challenge, would be any different. Especially as the exercise-heavy heel and sidekick Sunny had just debuted with the company.

Ship's hubris proved costly, though, as Horowitz caught him mid-push-up and rolled him up for the win.

Horowitz got a brief push out of it but it was not long before he was back on the undercard, putting others over as he had throughout the late 1980s and the first half of the 90s.

In hindsight, the idea of a newcomer with a ballroom dancing gimmick would conceivably beat a sure-fire Hall of Famer like Chris Jericho in his first match, at WrestleMania nonetheless, is even more absurd than it was way back in 2013.

That is exactly what happened inside MetLife Stadium at the 29th Showcase of the Immortals as Fandango emerged from the company’s developmental abyss, where he spent years as Johnny Curtis, to defeat Jericho and kick off what many expected to be a significant run.

While that was not necessarily the case, it was an unforgettable moment for a competitor who gritted his way through bad gimmicks and missed opportunities to score an unforgettable win on the grandest stage his industry has to offer.

Fandango would be a fixture on the main roster for seven years after before his release as part of mass roster cuts in June of 2021, but not before creating some memorable moments with tag team partner Tyler Breeze as one-half of Breezango.

One of the most intriguing moments of the 2004 WWE Draft was the split of Shelton Benjamin and Charlie Haas, known collectively as The World’s Greatest Tag Team. The former headed to the Raw brand, where he wasted little time making an impression on WWE fans.

On the March 29 episode of the company’s flagship show, Benjamin battled Triple H. Expected to be a match that put Benjamin over as a plucky young star and future contender, the audience was stunned when the former collegiate wrestler pulled off the upset, pinning The Game and igniting what many thought would be the next great push for a rising young talent.

In some ways, it was.

Benjamin would go on to carve a role for himself in the midcard, routinely having the best match of many a show and highlighting his athletic abilities in early Money in the Bank Ladder matches. He would not ever truly have an opportunity to rise to the level of competition a win over Triple H would suggest was in the plans but he has still had a tremendous career that continues today.

Still, there is no denying that the victory over The Cerebral Assassin still ranks as one of his signature victories and a proof of what could have been.

To say that the Hollywood heel version of The Rock is one of the greatest characters in WWE history would be an understatement the size of The Great One’s massive ego. Tainted by his time in the spotlight, The Most Electrifying Man in Sports Entertainment was no longer The People’s Champion and had no problem telling that.

He also drew the ire of The Hurricane, WWE’s resident superhero and undercard fan favorite.

Together, they would create some hilarious moments in backstage vignettes written by Brian Gewirtz, leading to an in-ring showdown with The Great One on the March 10, 2003 episode of Raw.

The match was mostly dominated by The Rock, as expected, but ended with a twist when “Stone Cold” Steve Austin made his presence felt, distracting his WrestleMania XIX opponent and allowing the masked babyface to score the biggest and highest-profile victory of his career.

It was the perfect payoff to a side story that succeeded because of the undeniable chemistry between the performers themselves and the dynamic of the underdog babyface against the established, headlining, egotistical heel.

The 2002 Royal Rumble match will forever be remembered for Maven’s stunning elimination of The Undertaker. It completely caught the audience off-guard and garnered an enormous pop from fans. On the February 4 episode of SmackDown, he sought to make it two monumental upsets in a row as he challenged The American Badass for the Hardcore Championship.

As a straight-up singles match, it was a one-sided beatdown from an angry and vengeful force of nature against the young rookie who spoiled his world title aspirations. Luckily for the inaugural winner of WWE’s Tough Enough reality show, he would have help in his battle against the future Hall of Famer.

The Rock interfered late, laying out The Deadman and allowing Maven to score the win and his first title with the company. The fans reacted with the excitement expected whenever Rock appeared but also greeted Maven’s victory with considerable enthusiasm, his first triumph over Undertaker still fresh in their minds.

Maven never became the next big thing in WWE but he did ensure that his name would be etched in the history books, a rare rookie given the honor of going over the most celebrated Superstar in WWE history not once, but twice.

It is almost unimaginable that Sheamus’ only main roster victories prior to his WWE Championship win over John Cena at December 2009’s TLC: Tables, Ladders and Chairs pay-per-view came in singles matches against Jamie Noble and Finlay, in a multi-man tag match and a battle royal.

The Celtic Warrior was still very much an unproven commodity to fans of Raw and SmackDown when he set foot inside the squared circle for his showdown with Cena, but that did not stop WWE officials from forging ahead with him as their next WWE champ.

In a stunning outcome, Sheamus beat Cena in a Tables match to secure his first world title. The Florida Championship Wrestling and ECW reboot export had captured the top prize in professional wrestling despite having less than 10 matches on the company’s two most prominent brands.

It was the ultimate show of trust in a young star with a great look and a gimmick the company felt it could promote to success. In this case, it worked.

Sheamus is a multiple-time world champion, a sure-fire Hall of Famer and at the age of 44, is having some of the best matches of his career here in 2022.

The idea of Owen Hart beating his brother, Bret, in 1994 was not that far-fetched.

The youngest Hart brother was in the middle of a significant push, his first shot at a legitimate main event run, and beating his sibling would provide him a considerable amount of credibility.

What shocked the WWE fan base is when it happened.

In the opening match of WrestleMania X, Owen countered a victory roll attempt by his brother and pinned his shoulders to the mat for a stunning three-count. Stunning because later that same night, The Hitman would challenge for the WWE Championship and the idea of him starting his night with a loss was surprising, to say the least.

What resulted from it was one of the best storylines in company history.

Owen watched with jealousy in his eyes as his brother, the same man he had defeated earlier in the night, regained the WWE title and celebrated to close out the event. From there, he made it his goal to try and emerge from the shadows of The Excellence of Execution by dethroning him.

That story does not advance, nor does it reach the heights that it did, without Owen winning that first encounter. It can also be argued that the legacy The King of Harts left, as well as the countless fans he amassed over the years, can be traced back to his older brother believing in him and trusting his own star power to help make him.

There are many instances on this list of unlikely upsets that led to unforgettable moments but not necessarily the permanent elevation of the Superstar who scored said victory. That is not the case with the No. 3 entry on this list.

Prior to the May 17, 1993 episode of Raw, Sean Waltman was an enhancement talent and butt of a weekly joke. Every time he appeared on television, he had a different name. One week, he would be the Lightning Kid and the next, the Cannonball Kid. Another, he might just be The Kid.

It was under that moniker that he set foot inside the squared circle with Razor Ramon, a high-profile star in the evolving New Generation of WWE and a guy perceived as a main event talent. He had just challenged for the WWE Championship four months earlier at the Royal Rumble after all.

The match looked like a squash match on paper, a one-sided affair that would highlight Ramon and give him a momentum-building win as the company moved into the summer months. Instead, a tough, resilient Kid caught a charging Ramon with a boot, climbed the ropes and delivered a moonsault press. Ramon, stunned, could not kick out in time and the lovable loser scored the biggest win of his young career and one of the most stunning upsets in WWE history.

The match and moment wowed the audience and started the build for Kid into a legitimate star in WWE. Ramon unselfishly put him over, did so again a few weeks later, and the young Minnesotan made the most of it. In two runs with WWE, he earned recognition as one of the best wrestlers in the world and is one of the few Superstars to be enshrined in the company’s Hall of Fame twice.

Bruno Sammartino was one of the most popular, beloved and greatest champions in WWE by the time 1971 rolled around. For eight years, he dominated the competition and established himself as the longest-reigning world champion in company history. His popularity was both widespread and cultural and it seemed rather inconceivable that anyone would come along that could conceivably knock him off his pedestal.

Especially Ivan Koloff, who was a serviceable heel, hated by the New York audience, but hardly a star on par with the reigning champ.

That is why his win remains one of the most shocking upsets in not only WWE history, but wrestling as a whole. The fans in New York were stunned, some openly crying over their hero's loss to the hated Russian villain.

It had, after all, been a very long time since Sammartino had lost in Madison Square Garden.

Koloff would turn around and drop the title to Pedro Morales, who would lose it to Stan Stasiak, before Sammartino regained it for another lengthy run.

The idea of Brock Lesnar being the underdog against any man is laughable but as he arrived at WrestleMania XXX for his match against The Undertaker, it was not a man he was up against.

The Phenom's unbeaten streak on wrestling's grand stage had grown to mythical proportions, a seemingly unconquerable mission that legendary competitors had embarked on 21 times but, ultimately, succumbed to.

Lesnar was not the guy to do it.

Until he did.

The images of flabbergasted fans, their mouths agape in awe as they realized what had just happened are now iconic. Mainstream outlets covered the stunning outcome and The Phenom, and what he meant to WWE, would never be the same as the last bit of intrigue and luster wore off with the referee's third slap of the mat.

To this day, Lesnar's unexpected win remains the greatest upset in WWE history, a moment in time unlikely to be matched and a win that is still debated.