Sports. Honestly. Since 2011

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

2. Shawn Michaels

The WWE Championship was the only championship missing from Shawn Michaels’ resume. The Heartbreak Kid entered the 1995 Royal Rumble match from the unenviable number one spot. However, it was a masterclass from Michaels, as the iconic one-foot-touching-the-floor spot was born at the ’95 edition of the Rumble.

Michaels eliminated eight wrestlers, lastly The British Bulldog, to win the 1995 Royal Rumble match. He became the first man to win the Rumble from the number one position.

Michaels was unable to unseat Diesel for the WWE Championship at WrestleMania 11. A year later, the Heartbreak Kid was desperate for the Boyhood Dream to come true. Furthermore, Michaels had a stellar performance in the 1996 Royal Rumble match. He managed to eliminate eight wrestlers for the second consecutive year.

He got some revenge by dumping Diesel over the top rope to win his second consecutive Royal Rumble match. Michaels’ Boyhood Dream came true as he defeated Bret Hart for the WWE Championship in a 60-minute Iron Man match at WrestleMania 12.

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.