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A photo of multiple-time WWE Royal Rumble winner Shawn Michaels.
January 26, 2026 By  History, WWE, WWE Universe

The 5 Best Multiple-Time WWE Royal Rumble Winners, Ranked

The WWE Royal Rumble is traditionally the start of the long, arduous road to WrestleMania. Since 1993, the winner of the Royal Rumble has been awarded a world championship match at WrestleMania. Three decades after the first Royal Rumble match, the women’s Royal Rumble match was introduced.

However, since 2018, wrestling fans have been treated to not just one but two Royal Rumble matches. For sure, some years the winner of the Royal Rumble is predictable, but some years it’s hard to call, especially with Jey Uso’s triumph in 2025.

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5 WWE Wrestlers Who Won the Royal Rumble in their First Attempt

Winning the Royal Rumble once is a phenomenal achievement, but some wrestlers have managed to win the Royal Rumble multiple times. Charlotte Flair made history in 2025 by becoming the first woman to win multiple women’s Royal Rumble matches, coupled with her 2020 triumph. Furthermore, 10 men have won the men’s Royal Rumble match more than once. This article will review the five best multiple-time Royal Rumble winners based on their performances in those titular bouts.

5. Edge

Edge was one-half of the Unified WWE Tag Team Champions alongside Chris Jericho when he tore his Achilles tendon in the summer of 2009. However, the Rated-R Superstar relinquished the Unified WWE Tag Team Championship.

Nevertheless, Edge made a surprising return as the 29th entrant in the 2010 Royal Rumble match. He eliminated his former tag team partner, Y2J, and a familiar rival in John Cena to win the 2010 Royal Rumble match in a seven-minute cameo.

After an emotional return to WWE in the 2020 men’s Royal Rumble match, Edge targeted victory in the 2021 men’s Royal Rumble match. However, he entered from the uneviable number one position. The 11-time world champion kicked things off with his former tag team partner and rival, Randy Orton.

Nevertheless, Edge eliminated Braun Strowman, Seth Rollins, and Randy Orton to win the 2021 men’s Royal Rumble match, 11 years to the day from his 2010 win. Unfortunately, for Edge, he became the first two-time Rumble winner to lose both of his world title matches at WrestleMania.

About Tevon King

Tevon is a big fan of professional wrestling since the days of the Attitude Era. His favorite wrestlers of all time are Edge, Chris Jericho, and Shawn Michaels. Currently he is a fan of Seth Rollins, Bayley, and Liv Morgan.

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