Also, Brock Lesnar was in nine SummerSlam main events, with six of those being back-to-back (2014-2019). That is the record for most main events in SummerSlam history (in case anyone was about to ask Ryan Byers about that). 10-year-old me’s fantasy booking aside, this is a great match. 4: The Undertaker vs Edge – Hell in a Cell – 2008Speaking of Edge being a great heel, two years later we have another Edge SummerSlam main event, and a third one for The Undertaker. I think with time, this will be looked back on as a classic SummerSlam match.