5 times a heel won a major WWE feud

#4 CM Punk vs Jeff Hardy

CM Punk and Jeff Hardy

At Extreme Rules 2009, Jeff Hardy defeated Edge to win the World title in a Ladder match. Moments later, CM Punk came out and cashed in his MITB briefcase on an exhausted Hardy, turning heel in the process. Punk and Hardy went on to have a lengthy feud, with Punk targeting Hardy's troubled past involving drugs.

Hardy won back the title at Night of Champions. At SummerSlam 2009, the duo met again in a TLC match for the World title. This time though, Punk managed to topple Hardy and grab the coveted prize again. On the following episode of SmackDown, Hardy challenged Punk for the title, inside a Steel Cage. Punk defeated Hardy for the second time in a row. Hardy left the company after the match, as per the stipulation that was put into place. In reality, he had left to heal his injuries. Punk, a hated heel at the time, had stood victorious in the end, leaving a bad taste in fans' mouths.