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The team with the worst winning percentage in the history of MLB -- the 1899 Cleveland Spiders -- still managed to win 20 games out of the 154 they played that year. This dismal .130 winning percentage is so bad that it is extremely unlikely that any MLB team will do worse. The 1916 Philadelphia Athletics -- the third worst team in MLB history -- had a .235 winning percentage, 100 points better than the Spiders.

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