#2 Booker T (0 wins, 5 losses)
In fairness to Booker T, he has been involved in some very high-profile SummerSlam matches throughout his WWE career – but that doesn’t change the fact that he lost every single one of them.
His most famous encounter at the PPV came when he lost his WCW World Heavyweight Championship in the main event against The Rock in 2001.
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Then, between 2002 and 2007, the WWE Hall of Famer competed at four more SummerSlam events, losing a tag match with Goldust against Christian & Lance Storm in 2002 before failing to win in singles matches against John Cena, Batista and Triple H.
Edited by Amar Anand