The Chicago White Sox beat the Chicago Cubs in the 1906 World Series.
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The Chicago White Sox defeated the Chicago Cubs 4 games to 2 in the 1906 World Series, the third World Series to be played.
Short Answer: White SoxThe Chicago White Sox won three world series ... 1906, 1917, and 2005, while the Chicago Cubs have only won two ... 1907 and 1908.
The White Sox won their first World Series in 1906, beating the Cubs. The Cubs won their first the next year, 1907, by beating Detroit.
The Chicago White Sox have won 3 World Series Titles. (as of 2009) 1906: The White Sox defeat the Chicago Cubs 4 games to 2 in Chicago's one and only Cross-Town World Series matchup to date. 1917: The White Sox defeat the N.Y. Giants 4 games to 2 2005: The White Sox defeat the Houston Astros by sweeping the series, 4 games to none. Chicago celebrates its first Championship in 88 years.
The Chicago Cubs have played in ten World Series, winning two.Won (1907, 1908)Lost (1906, 1910, 1918, 1929, 1932, 1935, 1938, 1945)