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Top 15 Dumbest Stipulations in Wrestling History

When two wrestlers are engaged in a hot feud that’s igniting the territory, there will usually be a match with some sort of stipulation match to blow off the feud. Normally, these stipulations will be for a prestigious world title or a chance for a world title that bring fond memories to fans' hearts and minds.

However, then there are matches where the stipulation is so comical or terrible that they bring about looks of disgust on fans faces. If wrestling at its heart is about the struggle between good vs. evil, so it's natural to try and spice that up every now and again. So, sometimes, bookers think that a steel cage match has been done to death (and they have been but are genuinely always welcome), so they think there's a need to reinvent the wheel.

Wrestling has its roots in the Carnival / Sideshow / Vaudeville world where anything and everything went, so it’s no wonder that all kinds of bookers would try all kinds of ways to put a butt every eighteen inches. Here’s 15 dumb ways they tried.

13 Cry Baby Match

via tumblr.com

12 Custody of Dominick Ladder Match

via theoclardy.wordpress.com

11 The Title Can Change Hands on a DQ

via thetoplister.wordpress.com

10 Control of the Company

via ecwfrenchtribute.free.fr

9 Concrete Crypt

via dawrestlingboard.com

8 Pink Slip on a Pole

via wwe.com
via wrestlecrap.com

7 Flag Match

via dailywrestlingnews.com

6 Last Chance Challenge

via wrestlinginc.com

5 Loser Wears A Dress

via forum.wrestlingfigs.com

4 Loser Has to Work for Winner

via wwe.com
via sportskeeda.com

When D-X split up in 1999, X–Pac and Road Dogg fought Chyna and Billy Gunn for the rights to the D-X name and brand, in a snoozefest of a feud with a ridiculous stipulation for the last match.

3 Loser Goes to Jail (Mountie vs. Bossman)

via prowrestling.wikia.com

2 Gulf of Mexico Match (Chavo vs. Punk)

via wwe.com

1 Kiss My (Insert Body Part Here) Match

via my123cents.com

The dumbest stipulation ever is a humiliating loss for the fans as well. It’s hard to convince non–watching friends how viable this sport is when WWE continues to have matches where the loser has to kiss the winner’s ass. Even worse was watching build–up to the anticipated Bret Hart/Jerry Lawler Kiss My Foot Match, where we had to sit through Lawler putting his feet into the grossest things imaginable. At least the match was good and Lawler wound up kissing his own foot. A worse match happened almost 20 years later when Michael Cole had to kiss the King’s foot, dipped in J.R.’s BBQ sauce.

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Top 15 Dumbest Stipulations in Wrestling History