#2 Mr. Perfect almost won the 1990 Royal Rumble match
"Mr. Perfect" Curt Hennig was one of the finest wrestlers of his generation, and according to IMDb, Mr. Perfect was scheduled to win the Royal Rumble match in 1990.
While it has been speculated that Hulk Hogan lobbied hard for himself to win the bout, it was ultimately Vince McMahon who made the call. In the end, The Hulkster got the win, ironically, by last eliminating Curt Hennig.
Though no championship shot was on the line, a victory in this contest could have been another accolade on Mr. Perfect's Hall of Fame resume. It was Hogan, though, who got the nod to aid in his push leading into that year's WrestleMania. At the biggest show of the year, he defended the WWE Championship against The Ultimate Warrior.
#1 CM Punk almost won the Royal Rumble match in 2008
Had John Cena not returned to the 2008 Royal Rumble at Madison Square Garden, CM Punk might have had his WrestleMania main event match.
One of Punk's ultimate desires in WWE was to main event The Showcase of the Immortals, and he almost had this opportunity early in his career with Vince McMahon's promotion. Punk later revealed on WWE Backstage on FOX that he was penciled in to win the match before Cena's return.
Cena had been out with injury, but he returned earlier than anticipated, which forced WWE's hand. They ultimately booked Cena to win the contest after he entered it as the thirtieth entrant. He went on to compete in the high-profile WWE Championship match at WrestleMania 24.
Despite this setback, CM Punk still scored a big victory at WrestleMania by winning the Money in the Bank Ladder Match.