The Chicago Cubs have not won a World Series since 1908.
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∙ 13y agoparshaves
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That would be his current losing streak of 104 races.
Michael Waltrip had the longest losing streak before winning at the Daytona 500 in 2001.
Pittsburgh pirates at 18 straight and counting
New Jersey Nets with an 0-18 losing streak
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In 1997, the Cubs started the season 0-14, with the 14 game losing streak being their longest ever.
The Phillies lost 23 games in a row in 1961.