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86 year World Series DroughtThe Boston Red Sox went 86 years without winning a World Series title from 1918-2004 but the Chicago Cubs holds the record with the longest World Series drought. As of 2009 the Chicago Cubs have not won a title in 101 years. The Last World Series title the Cubs won was in 1908. They also won in 1907 for a total of two World Series titles in franchise history.
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