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#10 The Undertaker wins his first Royal Rumble in 2007
The iconic WWE career of The Undertaker became even more legendary when he won his first Royal Rumble match in 2007. The Deadman entered his first Rumble match in 1991, and he was long overdue for a major victory in the contest.
The Phenom also became the first entrant to win the match, entering at number 30. He ultimately eliminated Shawn Michaels, who would become his WrestleMania rival a couple of years later.
They became the last two men in the bout and went back-and-forth for a heart-stopping ten minutes, before The Undertaker hammered the final nail in HBK's Rumble coffin by sending him crashing over the top rope.
#9 Cactus Jack, Dude Love and Mankind enter the 1998 Royal Rumble match
Mick Foley entered the Rumble match not just once in 1998, but three times overall. Known for his plethora of incredible personas, Foley entered the match at different stages using his different monikers - Cactus Jack, Dude Love and Mankind.
Despite having three opportunities to go all the way and rubber stamp his ticket to WrestleMania, he sadly fell short. However, the moment will go down as one of the craziest moments in Rumble history, seeing the "Three Faces of Foley" entered the match.
