#3 Booker T
Booker T’s most notable accomplishment is that he is a five-time WCW World Heavyweight Champion, but a lesser known record that he has to his name is that he is a five-time loser at WWE’s ‘Biggest Event of the Summer’.
Booker has faced some of the industry's biggest names at SummerSlam, including Triple H and John Cena, yet has come up short on every occasion. He even lost when teaming with Goldust against the Un-Americans back in 2002.
His most memorable appearances at the event were arguably against Batista in 2006 or his SummerSlam debut against The Rock. But having lost on every occasion, I’m sure Booker would rather talk about his World Title reigns than his Summerslam matches.
Edited by Nishant Jayaram