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#3 CM Punk failed to defeat Triple H
In 2011, CM Punk was chasing the WWE Championship but was failing at his every attempt. He claimed (kayfabe) it was because of Triple H who was using his strong position in the company to keep him away from the championship. But Triple H disagreed and a feud between the two men quickly ignited.
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Punk and Triple H had their first match at the Night Of Champions. While Punk initially thought he would get a chance to score a win over Triple H that would help his career get a push, surprisingly, the opposite happened. At the pay-per-view, Triple H defeated Punk in humiliating fashion and the latter couldn't digest it.
Is this man the funniest man in wrestling?
He questioned "The Cerebral Assassin" as to why he didn't put him over when it would've been best for the business. However, Punk didn't find an answer that could make him understand it and decided to go a separate route from Triple H.
A few years later, Punk got another opportunity to face Triple H at WrestleMania 30, but he didn't jump on it. Instead, he left WWE in a controversial fashion. To this day, Triple H remains one of the stars Punk failed to defeat one-on-one in WWE.
