#4 Kurt Angle (5 wins, 1 loss)
Considering he only competed at six SummerSlam events during his initial run with WWE, Kurt Angle has carved out a surprisingly impressive record for himself at the annual August PPV.
The Olympic gold medallist wasn’t able to win his first match at “The Biggest Party of the Summer”, losing a Triple Threat World Heavyweight Championship encounter against The Rock (Triple H was also in the match), but he then went on to win in five consecutive years at the show.
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In 2001 and 2003, he retained the World Heavyweight Championship against Steve Austin and Brock Lesnar, respectively, while he was also victorious in singles matches against Rey Mysterio, Eddie Guerrero and Eugene.