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#5 The Undertaker — 8 wins, 6 losses
The Undertaker is synonymous with WrestleMania, but he’s also synonymous with Hell in a Cell.
He has featured in 14 cell matches -- five more than anybody else -- and picked up eight wins, six losses and countless memorable moments along the way.
Mankind (who can forget?!), Kane, Big Boss Man, Randy Orton, Edge, CM Punk, Triple H and Shane McMahon have all felt the wrath of “The Deadman” inside the cell, while he has been defeated by Shawn Michaels, Kurt Angle (Armageddon six-man), Brock Lesnar x2, Batista and Kane.
His last defeat inside Hell in a Cell came at the 2015 event against Lesnar -- an encounter was later voted WWE's Match of the Year. Not bad for a then-50-year-old!
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