#2: Randy Orton (Six losses)

At SummerSlam 2004, Randy Orton became the youngest World Heavyweight Champion in history, and though that August night clearly went in the Legend Killer's favor, the same can't be said for most years. Instead, Orton currently has six losses at Summerslam, a poor record when you consider the Viper's truly epic career, which has seen him capture 13 World titles.
In fairness to the two-time Royal Rumble winner, Orton has been defeated by some of WWE's biggest names, with losses against the likes of John Cena, Brock Lesnar, Sheamus, Triple H, Roman Reigns and Hulk Hogan to his name, which might make his poor record look a little better.
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With a poor record like this, The Viper will be no doubt hoping to change things next Sunday, when he faces Kofi Kingston at the Pay Per View for the New Day star's WWE Championship.