WWE Superstars with the most Hell in a Cell appearances 

#3 Former WWE Champion Randy Orton (8 appearances)

The Viper has entered the Hell in a Cell structure eight times during his WWE career

14-time WWE World Heavyweight Champion Randy Orton has faced off against some of the most iconic names inside Hell in a Cell.

The Viper's first appearance inside the demonic structure came in a defeat against The Undertaker at the Armageddon 2005 pay-per-view event. This served as the final chapter of The Deadman and The Legend Killer's iconic feud on WWE television.

Orton's next appearance inside the structure came four years later when he defeated John Cena to become WWE Champion during the inaugural HIAC pay-per-view event. This was then followed by a successful WWE Championship defense against Sheamus inside Hell in a Cell the following year at the same event.

However, at HIAC 2021, Randy Orton was decisively defeated by Mark Henry, allowing the latter to retain his World Heavyweight Championship in the process.

Two years later, Orton would once again strike gold inside the structure as he defeated Daniel Bryan due to interference from Special Guest Referee Shawn Michaels. This allowed Orton to win the vacant WWE Title.

The Legend Killer squared off against long-term rival John Cena once again inside Hell in a Cell during HIAC 2014. However, Orton was unsuccessful in defeating Cena, allowing the Cenation Leader to become the No.1 Contender for the WWE World Heavyweight Championship.

Randy Orton's final two Hell in a Cell appearances were both wins. He defeated Jeff Hardy inside the demonic structure in HIAC 2018 and captured the WWE Championship from Drew McIntyre during the same event last year.