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I briefly considered one of those but ran into the same problem you had, it always ends up with a guy with no matchesBtw... I dunno if you'd considered this yet, Sky, but what about some bad things people "win"? Those "If you lose the Match, then X" Matches?
I started one of those earlier with Col. Robert Parker losing to Flyin' Brian in a "Loser has to wear a Chicken Suit" Match, which immediately ended because Parker's next win was against a Jobber, who only had one Match...