5 most successful gimmick matches in wrestling history

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Big Bossman in the infamous "Kennel from Hell" match in 1999.

#4 Hell in a Cell

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The first ever Hell in a Cell match was contested between the Undertaker and Shawn Michaels at Bad Blood 1997. The match was immediately a hit with fans.

Since 1997, 37 more matches in WWE have been contested inside the Hell in a Cell. Now every October it is the featured gimmick match on PPV. HIAC matches are also held outside this PPV as well, however.

The Undertaker holds the record with 14 HIAC matches, he has an 8-6 record in them. Triple H has won 6 matches inside the cell and lost 3. Batista, Brock Lesnar, Randy Orton, and Kevin Owens all have 2-0 records in HIAC matches and Shawn Michaels is 3-1. Poor Mick Foley has been involved in 4 HIAC matches and he's lost every single one of them.

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