10 Most Popular Heel Wins In Wrestling History

10. Randy Orton vs. Triple H (No Mercy 2007)

Randy Orton has always excelled far more as a heel than he has when portraying a babyface. Some guys are just better at playing one role, rather than ghosting between both. Triple H is another man who is typically better as a villain, but in late-2007, he was painted as a valiant competitor, desperately trying to defy all odds and taking on all-comers. At the No Mercy Pay-Per-View, HHH competed no less than 3 times. First, Triple H would vanquish Orton in the opening match on the card, but Mr. McMahon would then dictate that he still had to compete in a previously-scheduled match against Umaga. Defeating his second opponent, Triple H was then placed in a rematch against Orton in the main event, under 'Last Man Standing' rules. Even though fans were invested in the idea of Triple H overcoming such a massive set of obstacles in one night, they cheered big when Randy Orton won the belt. After nailing his rival with an RKO on top of the announcer's desk, Orton was able to return to his feet, but Triple H just didn't make it. Fans appeared thrilled by this, likely because it was an exciting match, but it was nonetheless intriguing to see the heel win be cheered.
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