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

Undisputed WWE universal champion Roman Reigns will make another defense of the top prize in professional wrestling at Crown Jewel on Saturday, this time against a social media celebrity with only two wrestling matches to his name.

Logan Paul will challenge The Tribal Chief in Riyadh, Saudi Arabia in a match that skews heavily in the the titleholder's favor. But what if the YouTuber accomplishes the unthinkable 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, potentially, the most memorable of them all.

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.

Yet, that is exactly what happened in front of their own eyes.

Santino Marella emerged from the crowd to knock off The Samoan Bulldozer and win the title in a huge upset, thanks in large part to the involvement of ECW champion Bobby Lashley.

Primarily utilized as a means to continue The All Mighty's rivalry with Umaga and the McMahon family, the segment launched Marella into stardom. He would go on to win the 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 on television and house shows against top stars, but he was always the guy tasked with making them look good.

There was no reason to believe his match with the Bodydonnas' 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.

Skip'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 wasn't long before he was back on the undercard, putting others over as he had done throughout the late 1980s and early 1990s.

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 in 2013.

But that's exactly what happened at MetLife Stadium when 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 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 flagship show, Benjamin battled Triple H. Expected to be a match that put the newcomer over as a future contender, the audience was stunned when he pinned The Game and ignited 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 have an opportunity to rise to the level of competition a win over Triple H would suggest, but he has still had a tremendous career that continues today.

Still, there is no denying that the victory over Triple H still ranks as one of his signature victories and 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 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 anyone 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, but it 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 and egotistical heel.

The 2002 Royal Rumble match will forever be remembered for Maven’s stunning elimination of The Undertaker.

It completely fooled the audience 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 a 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 his name would be etched in the history books as a 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 when he set foot inside the squared circle for his showdown with Cena, but that did not stop 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 pro 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 future Hall of Famer and is still having some of the best matches of his career here in 2022 at the age of 44.

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 give him a considerable amount of credibility.

What shocked the WWE fanbase 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 to emerge from his shadows by dethroning him.

That story does not advance 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 the victory. That isn't the case with the No. 3 entry on our list.

Prior to the May 17, 1993 episode of Raw, Sean Waltman was an enhancement talent and the 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 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 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 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 inconceivable that anyone could knock him off his pedestal.

Especially Ivan Koloff, who was a serviceable heel and 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 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 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 wasn't a man he was up against.

The Phenom's unbeaten streak on The Grandest Stage of Them All had grown to mythical proportions, a seemingly unconquerable mission that legendary competitors had embarked on 21 times but failed to conquer.

Lesnar was not the guy to do it. Until he did.

The images of flabbergasted fans, their mouths agape 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 unlikely to be matched and a win that is still debated.