Top 5 oldest Royal Rumble winners in WWE history 

Edge is not the oldest man to win a Royal Rumble match
Edge is not the oldest man to win a Royal Rumble match

#1 1999 Royal Rumble, Vince McMahon - 53 years and 5 months

Vince McMahon won the 1999 Royal Rumble
Vince McMahon won the 1999 Royal Rumble

There has been only one Royal Rumble winner above the age of 50, and he is the company's CEO, Vince McMahon. The 75-year-old won his only Royal Rumble Match 22 years ago at the Arrowhead Pond.

Mr. McMahon was the second entrant in the 1999 Royal Rumble match. His enemy Stone Cold Steve Austin was in the ring waiting for him in the initial phase of the 1999 Royal Rumble Match. Both Austin and McMahon escaped the squared circle and stayed alive in the contest until the very end.

In the match's final moments, Stone Cold Steve Austin eliminated Triple H, Owen Hart, and Big Boss Man to ensure that he and his boss were the last men remaining. The Rock, who was the WWF Champion at the time, proved to be the difference-maker in the battle royal.

The Rock distracted Stone Cold by taunting him with the world title in his hand. Mr. McMahon to capitalized, as he eliminated Austin from the bout. But when McMahon decided to renounce his chance of headlining WrestleMania, WWF Commissioner Shawn Michaels transferred this opportunity to the runner-up, Stone Cold Steve Austin.

McMahon tried his best to deny Austin a chance to main event WrestleMania. But his best efforts could not stop Stone Cold from becoming the WWF Champion at the "Showcase of the Immortals."

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Edited by Colin Tessier
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