#1. CM Punk never defeated Triple H one-on-one
CM Punk defeated many legends in WWE throughout his career, including John Cena and Chris Jericho. However, he never beat Triple H one-on-one.
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Punk was never shy about expressing his discontent with WWE management. Chief Operating Officer Triple H was one of the names Punk criticized during his time in WWE. It led to a feud that saw The Cerebral Assassin put his management position on the line in a no disqualification match against the Straight-Edge Superstar. Triple H promised to resign if he lost the bout.
The two men squared off at the WWE Night Of Champions pay-per-view in 2011. The Miz and R-Truth interfered in the match, attacking both competitors. Kevin Nash also interfered in the same manner before getting knocked out by Triple H. The King of Kings then pedigreed Punk to earn the victory.
That match was not the only one Punk had against Triple H. Earlier, he faced The Game on SmackDown in January 2010. He lost the match via disqualification after his Straight Edge Society followers, Luke Gallows and Serena, interfered.