WWE: The Top 15 Greatest Moments in Royal Rumble History

11. Mr. McMahon Wins The Royal Rumble Match: January 24, 1999

Arguably no rivalry in sports entertainment history was as profitable and more important than the Stone Cold Steve Austin vs. Vince McMahon rivalry.  It helped define the Attitude Era of the WWE and turned the tide in the bitter Monday Night War between the WWE and WCW.

This rivalry had too many memorable moments to count, but one, in particular, came at the Royal Rumble in 1999.  Austin and McMahon entered the Royal Rumble match at number one and number two respectively after then-commissioner Shawn Michaels overrode McMahon’s decision to enter the rumble at number 30.

McMahon went out under the bottom rope early in the match and used every trick in the book later in the match.  After finally returning to the ring after the match came down to him and Austin, McMahon got further help from The Rock.  The Corporate Champion taunted Austin with the WWE Championship belt just enough to distract The Texas Rattlesnake.

And while Austin was distracted, McMahon threw him over the top rope and won the Royal Rumble match.  It was a shocking moment that saw McMahon keep his promise that Austin wouldn’t win the Royal Rumble match.  Austin went on to main event WrestleMania anyways with The Rock, but this just furthered the rivalry between himself and The Chairman.

McMahon said Austin had no chance in hell to win the Royal Rumble in 1999, and by hell or high water, he was correct.