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#2 WWE COO Triple H (9 appearances)
Triple H is one of the most tenured Hell in a Cell performers in WWE history. The Game has defended the World Title multiple times inside the demonic structure and has faced off against some of the biggest stars in the business.
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Triple H's first appearance inside Hell in a Cell came at the No Way Out 2000. He defeated Cactus Jack (Mick Foley) to retain the WWE Championship and seemingly retire his opponent from in-ring competition.
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The Game's next appearance inside the hellish structure came during the infamous Hell in a Cell Match at Armageddon in 2000. Kurt Angle was able to defeat The Undertaker, Triple H, Stone Cold Steve Austin, Rikishi, and The Rock to retain the WWE Championship at the event.
Two years later, The Game once again competed in a Hell in a Cell match. This time, it was against WrestleMania X-8 opponent, Chris Jericho at Judgement Day 2002. Triple H was victorious over Y2J at the event.
From 2003-05, Triple H competed in all the three Hell in a Cell matches that took place in WWE.
The Game defeated Kevin Nash to retain the World Heavyweight Championship at Bad Blood 2003. This was followed by him defeating Shawn Michaels to retain the World Heavyweight Championship at Bad Blood 2004.
The Game's winning streak inside the structure was finally snapped by Batista at Vengeance 2005, allowing The Animal to successfully retain the World Heavyweight Championship.
Triple H's next two appearances inside Hell in a Cell came by teaming with HBK as a member of D-Generation X.
DX defeated Vince McMahon, Shane McMahon, and The Big Show in a 3-on-2 Handicap Hell in a Cell match at Unforgiven 2006.
This was followed by Triple H and Shawn Michaels defeating Cody Rhodes and Ted DiBiase in the main event of the inaugural Hell in a Cell pay-per-view in 2009.
The former WWE Champion's last Hell in a Cell match came at WrestleMania XXVIII against The Undertaker. The Deadman defeated The Game to not only end an era but also extend his mythic WrestleMania undefeated streak to 20-0.
