5 WWE stars with the most Hell In A Cell losses

#3 CM Punk — 2 wins, 3 losses

CM Punk has lost three Hell in a Cell matches

While CM Punk has two victories in Hell in a Cell matches, they both came towards the end of his WWE career — and both came against Ryback. Before then, he was 0-3 inside the steel structure.

The first of those three defeats was at the hands of The Undertaker, who took just 10 minutes to win the World Heavyweight Championship from “The Best In The World” at the inaugural HIAC pay-per-view in 2009.

At the 2011 event, Punk was pinned by Alberto Del Rio in a triple threat match for John Cena’s WWE Championship, and six days earlier, he was involved in a five-man dark match on Raw for Cena’s title which also took place inside the cell.