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#3 Shawn Michaels and Randy Orton - 3
Shawn Michaels and Randy Orton have won three Hell in Cell matches out of four and six encounters respectively. Orton defeated Daniel Bryan, Sheamus and John Cena while he lost to Mark Henry, Undertaker and ultimately to Cena. The match with Undertaker was an epic treat for the fans due to the intense build-up.
Shawn Michaels had a near to perfect win ratio, losing one out of four matches and that too against his D-Generation X partner, Triple H. Shawn Michaels defeated The Undertaker in the first ever Hell in a Cell match in the history of WWE! And his other two victories were in a tag team match with Triple H.
His most memorable bout was against Vince and Shane McMahon, where after losing the match, Vince had to put his face in a place that can't be mentioned.
