#3 Royal Rumble 1999: Vince McMahon won and forfeited his title shot

The rivalry between Vince McMahon and Stone Cold Steve Austin was at its all-time peak as the two men started the proceedings at the Royal Rumble match in 1999. Interestingly, Austin was the last man to be eliminated by the chairman. Hence, both the winner and the runner-up for the match clocked the same time of 56 minutes and 38 seconds.
Historical Impact:
The next night, Mr. McMahon forfeited his title shot against The Rock at WrestleMania 15 and became the first man in WWE’s history to do so. Notably, it was The Rock who helped him to eliminate Stone Cold the previous night.
In an interesting turn of events, the Rattlesnake got an opportunity to face the chairman of WWE, Vince McMahon, in a Steel Cage match at St. Valentine's Day Massacre - In Your House PPV. He went on to defeat the reigning WWF Champion, The Rock, at Wrestlemania 15.