Randy Orton
The list begins with the Apex Predator of the WWE who had the opportunity to enter the Hell in a Cell cage on seven different occasions. He won four of those matches three of which have been for the WWE Championship (Shawn Michaels was the special guest referee during his 2013 win). The last of his Cell appearance occurred, last year where he man-handled an aged Jeff Hardy with a mean-streak. It remains a true example of why he is a specialist in this kind of match. Apart from this, Orton pinned former world champs John Cena, Daniel Bryan, and Sheamus inside the structure that remains as a huge accolade.
Batista
The success rate is 100 percent for Batista inside Hell in a Cell. He walked into this on two different occasions to pick up victories. But most importantly, these wins came against the two most veteran competitors in this environment making it look even bigger. Batista pinned both Triple H and The Undertaker for the world heavyweight championship inside the Cell that marked the beginning of a top babyface run. It helped him carrying the Smackdown brand during the Ruthless Aggression Era which is why his name is a must in this list.
Shawn Michaels
The Heart Break Kidd competed in the inaugural Hell in a Cell match against The Undertaker at WWE Badd Blood in 1997. Despite the show-stealing performance by Michaels, the match was overshadowed by The Demon Kane's debut in the WWE. Later, HBK was given another opportunity to step into the structure against his best friend, Triple H where he lasted for 47:26 minutes proving he's an Ironman. Overall, Mr. Wrestlemania had four visits to Hell in a Cell securing three wins among them.
The Undertaker
The Phenome should have been listed on the first position among the top 5 WWE successful Hell in Cell performers. But his success rate is not up to the mark in this environment. Otherwise, the gimmick match is perfectly suited for his Demon of Death-Valley character that he plays, on-screen. The Undertaker had competed in 12 such matches that is the most number of entrances made by a WWE superstar inside Hell in a Cell. But he came up short in six of them taking his winning statistics to only 50 percent. But, on the other hand, gave birth to some infamous moments inside the structure by sending superstars like Mick Foley, Edge or Shane McMahon, ‘straight to hell.'
Triple H
Triple H earned the nickname of WWE's Cerebral Assassin for a reason since he possesses the highest success rate inside Hell in a Cell. He caused massacre inside this cage with companions like the sledgehammer, Evolution or DX members. Out of his nine appearances in this cage, he mastered opponents on six occasions against opponents like Cactus Jack, Chris Jericho, Kevin Nash, Shawn Michaels, Randy Orton and more. But it's the ‘End of an Era' match with The Undertaker at Wrestlemania 28 which stands out among all of them. No matter what, it will always be a benchmark performance in this genre.