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The Cubs have won just 2 World Series Titles (1907 and 1908) As of the 2010 season, it has been 102 years since their last World Championship! The longest drought in all professional sports history.
p.s. The Cubs won a Major League Record 116 regular season games in 1906 and were heavily favored to win the World Series that year. However, they lost 4 games to 2 to the Chicago White Sox who won not only their First of 3 Titles that season but brought Chicago its very first World Championship.
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Starting with 1908, the Chicago Cubs have been to 8 World Series: 1945, 1938, 1935, 1932, 1929, 1918, 1910, 1908
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