Triple H
The Cerebral Assassin of WWE is the undisputed kingpin when it comes to Hell in a Cell match. To be honest, he is one of the big reasons who made this gimmick match infamous by stepping into the structure and pulling off dominate wins, one after another. Overall, he competed in nine Hell in a Cell matches, coming out in 6 of them as the winner. Two of those wins were for being for the WWF Championship and the WWE World Heavyweight Championship. The other one was for the WWE Tag Team Championship with D-Generation X. But what keeps him in the first position of top 5 successful superstars in Hell in a Cell matches list is the outing with The Undertaker at WrestleMania 28.