I'm pretty sure only once, in 1908
The Cubs won three games in the 1945 World Series.
The Chicago Cubs have won two World Series, they won the 1907 and 1908 World Series against Detroit however in 1907, it was won with Chicago winning four games and in the 1908 World Series, the Chicago Cubs won the series in five games.
In the 1918 World Series, the Red Sox defeated the Cubs four games to two.
The Chicago Cubs have won two World Series, they won the 1907 and 1908 World Series against Detroit however in 1907, it was won with Chicago winning four games and in the 1908 World Series, the Chicago Cubs won the series in five games.
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The Cubs have but 2 World Series Titles. 1907 and 1908 The Cubs went to the Series in 1906 as well but lost it in 6 games to the superior White Sox. As of 2010 the Cubs are in the midst of a 102 year Championship drought. The longest such drought in all of sports! They haven't appeared in a World Series since 1945.
The Cubs record in the 1906 National League was 116-36, but lost to the White Sox four games to two in the World Series.
The Cubs won 2 World Series in 1907 and 1908
The Cubs last won the World Series in 1908. Since then, the Yankees have won 26 World Series.
The Chicago Cubs won two World Series titles in 1907 and 1908.
The Cubs Never won the world seires but the played in it .
The Chicago Cubs have won two World Series titles. The last was in 1908, the other in 1907. In 1907 they beat the Detroit Tigers 4 games to 0, and in 1908 they again beat the Tigers 4 games to 1.