5 most surprising Royal Rumble winners

#4 Vince McMahon - 1999

''You're going to the main event of WrestleMania''... Almost

Heading into the 1999 Royal Rumble match, the popular opinion was that WWE's biggest star 'Stone Cold' Steve Austin would win his 3rd consecutive Royal Rumble match and face The Rock for the WWE Championship in the main event of WrestleMania XV. Although the WrestleMania main event happened, Austin didn't get there the way everyone expected him to.

Steve Austin had been the only major star at that time to be competing in the Rumble match. Although it would feature the like of former WWE Champion Kane and future World Champions Triple H, Jeff Jarrett, Edge and Ken Shamrock, there were really no other believable winners in the match other than Austin. They had been building up to Austin getting Vince McMahon alone in the ring and beating him senseless for months, so everyone thought it would be just that before a Stone Cold win, but what we got instead was a shock Rumble win for the owner of WWE as he eliminated Austin with the help of The Rock.

As expected, Vince would later lose his Championship match to Austin in a stipulation Cage match at the St. Valentines Day Massacre pay-per-view.