In professional wrestling, the art of a major upset victory tells a compelling story. WWE, with its decades of dedication to storytelling, has delivered some of the most memorable surprise wins in wrestling history. Fans experience genuine shock and awe during these unforeseen moments, making them deeply engaging.
The greatest upset victories stand the test of time, still evoking strong emotions when revisited. Audiences become genuinely invested, and what defines an exceptional upset victory is the profound impact it has on fans, lingering long after the event. Each of these WWE surprises continues to resonate due to the raw astonishment they created.
10. Owen Hart vs. Bret Hart – WrestleMania 10 (March 20, 1994, 20:21 minutes, fan rating 9.46)
Bret Hart, WWE’s top star and fan favorite, headed into WrestleMania 10 in a unique situation where both he and Lex Luger earned title shots by simultaneously eliminating each other in the Royal Rumble. Owen Hart, Bret’s younger brother, faced him in the opening match. No one anticipated Owen’s victory, but he secured a clean pin in a genuinely shocking moment.
9. Kevin Federline vs. John Cena – Monday Night Raw (January 1, 2007, 4:55 minutes)
In the late 2000s, John Cena rarely lost to fellow top wrestlers. WWE booked Kevin Federline, Britney Spears’ ex-husband, into a feud with Cena fueled by pop culture disdain. Cena was surprisingly defeated on TV due to interference from his rival Umaga, who attacked him. This loss, although never erased from Cena’s record, intensified their rivalry.
8. Eddie Guerrero vs. Brock Lesnar – No Way Out 2004 (February 15, 2004, 30:07 minutes, fan rating 8.94)
Well-orchestrated upsets can be more effective than impromptu shocks. At No Way Out 2004, Eddie Guerrero challenged Brock Lesnar for the WWE Championship. The build-up made fans believe Guerrero could pull off a surprise win. His victory was filled with genuine emotion, marking one of WWE’s greatest moments.
7. Kalisto vs. Alberto Del Rio – Monday Night Raw (January 11, 2016, 15:14 minutes, fan rating 6.62)
Alberto Del Rio, a favored wrestler in WWE, was unexpectedly defeated by Kalisto in a live match for the US Championship. Fans expected a straightforward title defense from Del Rio, especially since Kalisto hadn’t been pushed significantly. This upset highlighted the peak of Kalisto’s WWE career.
6. Barry Horowitz vs. Skip – SummerSlam 1995 (August 27, 1995, 11:21 minutes, fan rating 5.28)
Barry Horowitz is famously known as a top enhancement talent used to elevate bigger stars. At SummerSlam 1995, Horowitz surprisingly defeated Skip (Chris Candido), marking Horowitz’s first major win after a long losing streak, catching fans off guard.
5. Hurricane vs. The Rock – Monday Night Raw (March 10, 2003, 9:31 minutes, fan rating 7.17)
During The Rock’s popular “Hollywood Heel” phase, he engaged in a comedic rivalry with the Hurricane. Fans enjoyed the humor so much that The Rock requested a singles match, where interference from Steve Austin allowed Hurricane to secure the surprise win, making it one of the top upset moments.
4. Maven vs. The Undertaker – SmackDown (February 7, 2002, 6:34 minutes, fan rating 5.50)
Although Maven’s elimination of The Undertaker in the 2002 Royal Rumble is well-remembered, their singles match on SmackDown saw another surprise when Maven defeated Undertaker to win the hardcore championship, doubling down on the shock.
3. Shelton Benjamin vs. Triple H – Monday Night Raw (March 29, 2004, 19:56 minutes, fan rating 7.60)
Following the WWE brand split draft, Shelton Benjamin was pushed as a singles competitor and challenged Triple H on Raw. Benjamin stunned audiences by executing a quick pinfall win over Triple H, marking the height of his early WWE singles career.
2. Sheamus vs. John Cena – TLC 2009 (December 13, 2009, 16:20 minutes, fan rating 5.66)
Sheamus, newly drafted to Raw in 2009 and fresh off the ECW brand, received a major push opposing John Cena for the WWE Championship. WWE booked a historic upset where Sheamus defeated Cena, becoming the new WWE champion without Cena being pinned.
1. 123 Kid vs. Razor Ramon – Monday Night Raw (May 17, 1993, 2:12 minutes, fan rating 6.00)
Among the greatest upset moments, the relatively unknown 123 Kid (Sean Waltman) faced established mid-card star Razor Ramon in a main event. WWE expected fans to find the obvious winner boring, but 123 Kid’s surprising victory remains one of WWE’s most iconic upsets.
Fan Take: These shocking upset victories are essential to WWE storytelling as they keep fans emotionally engaged and invested in the unpredictable nature of wrestling. Such moments not only create lasting memories but also shape the future trajectories of wrestlers and the sport itself.
