15 Biggest Losers In WWE SummerSlam History

While all the previous entrants who've shared five losses had one thing in common (they’d picked up victories along the way), the same cannot be said for the ever-unlucky Jeff Hardy.

Not that he’d want to, but Jeff can make the tragic claim of being 0-5 at SummerSlam. Although at least that’s not quite as bad as his 0-6 record at WrestleMania, but I digress...

It’s still not great though and, fittingly, his turmoil began with a Tag Team Turmoil match in 1999, before he teamed with his brother Matt once again as they lost in TLC action just one year later. The two then went their separate ways, but it didn’t bring a change in fortunes. Jeff lost the Hardcore title to Rob Van Dam in a Ladder Match in 2001, before MVP beat him in ’08, and the previously-mentioned CM Punk emerged the victor in their TLC match in ’09.

With those two TLC matches to his name, at least Jeff can say he’s created some awesome SummerSlam moments. Other than that, though, there’s not really a lot for him to shout about.