WWE: 10 Greatest Moments Of Austin Vs McMahon Feud

7. 1999 Royal Rumble

We couldn't have the match at St Valentine's Day Massacre without having the 1999 Royal Rumble match, with Vince rigging a drawing to have Austin enter in the first spot. His plan backfired a bit, though, as then-commissioner Shawn Michaels entered Vince with the second spot. This led to some hilarious vignettes of Vince training for the Rumble, with Shane McMahon helping him as he tried to catch live chickens and ran behind a limousine with Shane yelling encouragement at him through the vehicle's sunroof. Their participation in the match itself was brief and spotty, to say the least. After starting the match with some stalling, Vince ended up luring Austin to the restroom in a chase, where Austin was then jumped by Vince's Corporation goon squad. As Austin was placed in an ambulance, Vince would make his way back to the ring, but for commentary, even though he was still in the match. Of course, no kayfabe happiness for Vince McMahon can last very long, and sure enough, this didn't, either, as Austin would return to the arena... driving the ambulance. Trust me, folks... I'm not sure how Austin avoided prison time, either. https://www.youtube.com/watch?v=E_fu5C2804w Austin was caught in the match while Vince remained on commentary, but it eventually came down to just them remaining. The first two entrants were the last two entrants. After some distractions by then-WWF Champion, The Rock, Vince was able to shock the world and dump Austin over the top rope to win. It wasn't the best performance in the Rumble's illustrious history, but it goes down as one of the most memorable, that's for sure.