The Chicago Cubs have won just two World Series Titles. 1907 and 1908. They won a major league record 116 games in 1906 and were heavily favored to win it all that year but they lost the World Series to the Chicago White Sox 4 games to 2.
The 2010 baseball season marks the 102nd anniversary of their last World Series Championship. It is the longest drought in ALL of Sports History.
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The Chicago Cubs have won two world series the first was in 1907 when they faced the Detroit Tigers and won 4 games to 0 and in 1908 they again faced the Detroit tigers and won 4 games to 1.