5. Steve Austin – 1999
In 1999, Steve Austin was bidding to make history by becoming the first man to win three Royal Rumble matches consecutively. However, Mr. McMahon dumped Austin over the top rope to win the Royal Rumble match, all thanks to interference from his Corporate Champion, The Rock. Nevertheless, Austin had the last laugh as he beat McMahon in a steel cage match at St. Valentine’s Day Massacre to become the new number one contender for the WWE Championship.
Austin and Rock slugged it out in the first of their three WrestleMania encounters at WrestleMania 15 with the WWE Championship on the line. Their match was brilliant, and Austin curtailed Rock’s WWE Championship reign to become a three-time WWE Champion. McMahon didn’t have his first WrestleMania match at this event; instead, he looked on in horror as his sworn enemy stood tall with the WWE Championship.
