#3 Winning the Royal Rumble
CM Punk competed several times in the Royal Rumble PPV. However, he could never win a Royal Rumble match. This is a big blot in his otherwise successful career in WWE. Punk deserved to win the Royal Rumble match. Unfortunately, this did not happen, and, WWE management should regret that forever.
Had Punk won a Royal Rumble match, it would have been a win-win situation for both WWE and Punk. He could have headlined WrestleMania and challenged a Champion of his choice. That could have set the path for several new rivalries and feuds, which WWE failed to capitalize upon.
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Punk is one of those rare superstars, who has eliminated a female superstar at the Royal Rumble. He eliminated Beth Phoenix, at the 2010 Royal Rumble match. Even though Punk has a good record at Royal Rumble PPV, winning the Rumble match would have been an excellent accomplishment for Punk.