10 times heels won at WrestleMania

#4 Triple H (WrestleMania XIX)

Booker T versus Triple H at WrestleMania XIX

The match between Booker T and Triple H at WrestleMania XIX is one that was marred by controversy. The Game was the heel, as he so often has been throughout his career, and was accused of bringing Booker's race into the equation during the build to their match.

With that in mind, it was assumed by many that Booker would get the win when they finally faced off. That was not the case of course otherwise this match wouldn't have made the list. Triple H won the bout and retained his World Heavyweight Championship.

Like Yokozuna The Cerebral Assassin needed the heel help of a friend to ensure he left with the championship. Ric Flair was at ringside and it was him slamming Booker's knee into the steel steps that started the ball rolling on Triple H's win that year.