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The worst I can find in the modern era (post 1901) is a 21-21 by Bill Dineen while pitching for Boston Americans in 1902.
The most recent "worst" 20 game winners are knuckleball pitchers Wilbur Wood, 24-20 for the 1973 Chicago White Sox and Phil Niekro 21-20 for the 1979 Atlanta Braves
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