15 Biggest Losers In WWE SummerSlam History

8. The Undertaker (5 Losses)

Out of the four loss club now and into some rather elite company as The Undertaker is our next entry on this list.

The first of his five defeats arrived in the novel Boiler Room Brawl with Mankind at SummerSlam 1996. Successive WWE Championship defeats then followed, first to Bret Hart in ’97 and then against Stone Cold Steve Austin in ’98.

It would be another six years before he lost again at the PPV, though, after JBL beat him via DQ in a World title match in 2004. And then his most recent shortcoming came the following year when a young legend-killing Randy Orton lived up to his billing with victory over the Deadman.

Still, there’s the small matter of ten victories to factor in along the way, an all-time record in itself. Highlights include his Hell in a Cell clash with Edge in 2008, and of course the score-settling meeting with Brock Lesnar just last year in 2015.

Ranking ‘Taker any higher than this would have been rather counterintuitive, given that incredible haul of wins he’s racked up.