3. Triple H - 13 Matches
It is no surprise to see Triple H near the top of this list, with a sensational thirteen matches at SummerSlam. You wouldn't bet against him extending that number even further in the future, even though he is now part time at 46 years of age. His appearances have been over several generations. He wrestled as Hunter Hearst Helmsley at the 1995 event, defeating Bob Holly. One of his first major matches was against The Rock at the 1998 event, in which he proved victorious in a good ladder match. A year later he was in the main event against Steve Austin and Mankind, and he has been there or there about ever since. His 2002 brawl with Shawn Michaels is undoubtedly his finest performance at the annual event.