10 Most Surprising WWE Royal Rumble Winners Ever

8. Mr. McMahon (1999)

In 1999, Vince McMahon was not viewed as even a part-time wrestler by the fans and audiences of WWE. He was a former ringside commentator who only recently began flaunting his real-life ownership of the company on-screen, and he had yet to step into the ring for a real, official match. He teased a couple matches on television and even participated in the Corporate Royal Rumble on RAW just prior to the '99 Rumble PPV, but fans were still curious about what they would see from the WWE patriarch when he stepped into the ring at the Royal Rumble. In addition to McMahon's lack of in-ring experience, fans expected the main event of WrestleMania XV to center around Steve Austin's quest to reclaim the title. Even in January, that seemed to mean an obvious main event match against The Rock which likely meant the 30-man battle royal would be won by Steve Austin for the third straight year in a row. Needless to say, the result came as a shock when the inexperienced and puffed up Vince McMahon secured the victory.
Contributor
Contributor

A former stuntman for Paramount Pictures, Matt enjoys sports, water skiing, driving fast, the beach, professional wrestling, technology, and scotch. At the same time, whenever possible. Having attended many famous (and infamous) shows including WrestleMania XV, In Your House: Mind Games, and the 1995 King of the Ring, Matt has been a lifelong professional sports and wrestling fan. Matt's been mentioned in numerous wrestling podcasts including the Steve Austin Show: Unleashed, Talk Is Jericho, and Something To Wrestle With Bruce Prichard. As a former countywide performer, Matt has been referred to as Mr. 300 for his amazing accomplishments in the world of amateur bowling. He is also the only man on record to have pitched back-to-back no hitters in the Veterans Stadium Wiffle Ball League of 2003.