Top 15 Greatest Upset Victories in WWE History

The underdog is an all-inspiring part of the sporting world. Each season - regardless of the league - there is seemingly that one Cinderella story. That one case which causes hearts to bleed and eyes

The underdog is an all-inspiring part of the sporting world. Each season - regardless of the league - there is seemingly that one Cinderella story. That one case which causes hearts to bleed and eyes to water. These underdogs help produce what has become widely known as "upset victories." For many, the upset is welcomed as it shines a new light on new faces. However, there are those who stand guard against the underdogs and their upsets with the general consensus being that the underdog does not belong.

Take a look at Super Bowl XLII: the New England Patriots had not lost a game all season and were set to play the New York Giants in the big game; a team who finished the regular season with a 10-6 record. The Giants were solid but far from great. The Patriots were great. However, in some cruel twist of fate, the Giants would take that Super Bowl away from the Patriots in one of football's all time greatest "upset victories." Imagine the violent vibe in the Boston air that night as a team from New York hoisted the Lombardi Trophy.

Well, the same can be said for wrestling fans ...

In this non-traditional athletic world, outcomes are determined before anybody ever steps foot inside a ring. This is understood - or should be understood - by those who tune into the squared-circle-melee. The common theme for many years would see bigger wrestlers succeed over the smaller performers. However, somewhere along the line, fans grew tired of the same old formula. The days of Hulk Hogan and The Ultimate Warrior were replaced with the Shawn Michaels and Bret Hart years, wrestlers who had smaller physics and who were better performers.

Collectively, Shawn Michael and Bret Hart have combined for eight WWE Championships while Michaels has also captured the World Heavyweight Championship once while the Big Gold Belt was part of WWE programming.

In this piece, we will take a look at those wins that have shocked the WWE audience over the years.

These are the top 15 greatest upset victories in WWE history:

15 Rey Mysterio Wins the Royal Rumble 


Event: Royal Rumble

Date: January 29th, 2006

The Royal Rumble match has long been a bout of barbarians where the bigger you are, the better the chance you have at survival. However, back in 2006, this concept was tossed aside in favor of a smaller competitor.

Rey Mysterio would enter the match from the #2 position and would have to outlast everybody. That night in Miami, Mysterio would spend 1:02:12 in the match (an all time record) to earn a title shot at WrestleMania.

This would prove to be the biggest upset in the history of the Royal Rumble.

14 Carlito Over John Cena 


Event: SmackDown

Date: October 7th, 2004

In the fall of 2004, the future of WWE was certain: John Cena was going to be the next guy who carried the company. While working exclusively on SmackDown at this time, Cena served as United States Champion.

Then one night, in his own backyard, John Cena would place the strap on the line against a debuting Carlito Caribbean Cool. In a first-impression twist, Carlito would cheat his way to the United States Championship on his very first night.

John Cena would be forced to suffer the hometown humiliation.

13 Paige Over AJ Lee 


Event: Monday Night Raw

Date: April 7th, 2014

It was the night after WrestleMania XXX and a cocky AJ Lee - who had successfully defended the Divas Championship against thirteen other women the night prior - was out to boast about her brilliance.

Suddenly, the music of NXT Women's Champion, Paige, would hit and before long a Divas Championship match was taking place. Surely, AJ would not lose to the rookie in her first match, right? Wrong.

Paige would shock the crowd and AJ with the unexpected victory.

12 Shelton Benjamin Over Triple H 


Event: Monday Night Raw

Date: March 29th, 2004

Following WrestleMania XX, a talent draft would take place where Raw and SmackDown would exchange a number of Superstars. One of those coming over to Raw from SmackDown was Shelton Benjamin.

While known as a tag team wrestler, Shelton Benjamin was poised for a singles run and would begin this journey with a match against the biggest star in WWE at the time, Triple H. "The Game" was set to rip Benjamin apart in an easy contest.

However, Shelton Benjamin would score the shocking upset over Triple H.

11 Maven Over The Undertaker 


Event: SmackDown

Date: February 7th, 2002

This all began at the Royal Rumble where Maven - a Tough Enough winner - would enter the match and eliminate The Undertaker from the competition, which in its own right can be considered a major upset.

Obviously, this did not bode well with The Undertaker - who was Hardcore Champion at the time - and would later face Maven for the mangled belt. The Undertaker had the most evil of intentions but Maven would pull through thanks to The Rock.

While help was needed, this victory is still considered massive upset.

10 Kevin Owens Over John Cena 


Event: Elimination Chamber

Date: May 31st, 2015

This match remains fresh in the minds of the WWE Universe as the NXT Champion, Kevin Owens, would Challenge the United States Champion, John Cena, in his debut match on the main roster.

Children in attendance would shed tears in Texas that night as the brash newcomer would step into the ring with the face of WWE and defeat the Almighty John Cena without any tricks or dirty tactics.

This is by far the biggest WWE upset in recent memory.

9 Rico Over Ric Flair 


Event: Monday Night Raw

Date: September 16th, 2002

Rico is more-or-less a forgotten relic from the Ruthless Aggression Era. He was a stylist/manager who one day found himself on the big stage of Monday Night Raw and in a match against the greatest of all time in Ric Flair

Ric Flair may have been a lot older but the "Dirtiest Player in the Game" was never going to lose a match to a guy like Rico; it just wasn't going to happen ... until it did. Rico with a surprise kick actually pinned Flair for the three count.

This upset was without question the biggest victory of Rico's career.

8 1-2-3 Kid Over Razor Ramon 


Event: Monday Night Raw

Date: May 17th, 1993

Perhaps this wouldn't have happened if the participants involved were not esteemed member of "The Kliq." Nevertheless, Scott Hall was happy to put over his buddy Sean Waltman on an episode of Raw.

Working as Razor Ramon and 1-2-3 Kid, Hall and Waltman would compete in a match set to favor the larger Superstar. However, it was Kid who would pull a fast one over on Ramon and pick up the upset victory.

1-2-3 Kid had arrived as The Kliq were set to rule wrestling.

7 Sheamus Over John Cena 


Event: Tables, Ladder, and Chairs

Date: December 13th, 2009

The idea of a rookie coming in and going over on John Cena seemed preposterous in the winter of 2009. Which is why nobody gave Sheamus a fighting chance in a Tables match against Cena.

While it wasn't anything great or highlight worthy, John Cena would in fact fall through a table, awarding Sheamus not only the match but the WWE Championship in a Luck-of-the-Irish upset victory.

This night would jumpstart Sheamus' career as a WWE Superstar.

6 Mankind Over The Rock 


Event: Monday Night Raw

Date: January 4th, 1999

The WWE Championship was not entirely foreign to Mankind as his Mandible Claw had come close to grabbing the title in the past. However, on this infamous night, Mankind was about to finally grasp the gold.

While The Corporation stood in the corner of the WWE Champion, The Rock, D-Generation X stood in Mankind's corner. However, this victory was solidified by the shattering of glass as "Stone Cold" Steve Austin would help Mankind pull off the upset.

This title change played a significant role in the moment shift of the Monday Night War.

5 The Hurricane Over The Rock 


Event: Monday Night Raw

Date: March 10th, 2003

The stage was set for "Stone Cold" Steve Austin vs. The Rock at WrestleMania XIX. This would mark the third time (with Austin up 2-0) that the mega-stars would compete against each other at WrestleMania.

In the build towards this encounter, The Rock would find himself involved in a side feud with The Hurricane which would lead to a match and an unforgettable upset as The Hurricane - thanks to a distraction from Austin - would pin The Rock.

The Hurricane would never main event WrestleMania, therefore consider this his moment.

4 Chris Jericho Over Triple H 


Event: Monday Night Raw

Date: April 17th, 2000

Nowadays, watching Chris Jericho go over on Triple H would not be considered an upset. However, in the spring of 2000, it was just that as Jericho was still new to the WWE and Triple H had become a top star.

Chris Jericho would surprise everybody one Monday night when he defeated Triple H for the WWE Championship. However, Triple H would bully the referee into reversing his decision, thus nullifying the victory.

This would serve as a launch pad for Chris Jericho who proved he belonged at the top.

3 Jeff Hardy Over Triple H 


Event: SmackDown

Date: April 12th, 2001

There was never any doubt that Jeff Hardy would break free as a singles competitor in WWE and, in 2001, Hardy would make an emphatic statement by challenging then Intercontinental Champion, Triple H.

With the fans firmly in his corner, Jeff Hardy would go to war with the "Cerebral Assassin." Hardy would fight with a never-say-die attitude and eventually pick up the victory and the Intercontinental Championship over Triple H.

What a memorable night for the future WWE Champion.

2 Eddie Guerrero Over Brock Lesnar 


Event: No Way Out

Date: February 15th, 2004

One night removed from Valentine's Day and love would consume the air of the wrestling world as one of its most cherished performers would finally reach the heights to which he was destined.

Eddie Guerrero would challenge Brock Lesnar for the WWE Championship; and while some outside help from Goldberg was involved, it simply didn't matter to the fans who cheered in adulation as Guerrero captured the gold.

This night made everything worth while for Eddie Guerrero.

1 Rey Mysterio Over Kurt Angle and Randy Orton 


Event: WrestleMania 22

Date: April 2nd, 2006

This list will end where it began, with Rey Mysterio. That Royal Rumble victory which we alluded to early was only the beginning as Mysterio would do the unthinkable at WrestleMania 22.

The World Heavyweight Champion, Kurt Angle, would defend his belt against both Rey Mysterio and Randy Orton; who weaseled his way into the match. This would all lead to a dramatic and well-deserved finished.

Rey Mysterio would leave Chicago as the new World Heavyweight Champion.

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Top 15 Greatest Upset Victories in WWE History