The Chicago Cubs have won three World Series, in 1907, 1908, and 2016.
In addition to those championships, the Cubs have played in eight other World Series, all losses: 1906, 1910, 1918, 1929, 1932, 1935, 1938, 1945. The Cubs’ precursor, the Chicago White Stockings also played the St. Louis Browns of the American Association to a tie in the 1885 championship series, also titled the “World Series,” before losing outright to the Browns in the 1886.
Here is a rundown of each of those Cubs teams that won National League pennants, and the World Series they appeared in.
1906 World Series – Chicago White Sox over Chicago Cubs (4 games to 2)
The Cubs lost the Series in six games to the crosstown White Sox despite setting a record with 116 victories and a .763 winning percentage that still stands as the all-time record.
1907 World Series – Chicago Cubs over Detroit Tigers (4 games to 0; 1 tie)
After “falling” to 107 wins in the regular season and playing to a tie in Game 1 of the World Series, the Cubs swept Ty Cobb and his Tigers in Games 2-5 of the 1907 Fall Classic.
1908 World Series – Chicago Cubs over Detroit Tigers (4 games to 1)
The Cubs fell below 100 victories (with 99) for the only time between 1906 and 1910 but still managed to beat the Tigers in five games in the 1908 World Series. This year — 1908 — would become infamous for Cubs fans as their team failed to win another title for more than a century.
1910 World Series – Philadelphia Athletics over Chicago Cubs (4 games to 1)
After missing out on a pennant in 1909, the Cubs were back in the World Series in 1910, only to lose in five games to Connie Mack’s A’s.
1918 World Series – Boston Red Sox over Chicago Cubs (4 games to 2)
After an eight-year absence, the Cubs won another National League pennant, but fell to Babe Ruth and the Red Sox in the World Series. This Fall Classic is historic as the only Red Sox-Cubs WS matchup and the last time either team would win a title until Boston broke their “Curse of the Bambino” in 2004.
Both teams would get off the title snide in the 2000s with Theo Epstein at the helm of their baseball decision-making.
1929 World Series – Philadelphia Athletics over Chicago Cubs (4 games to 1)
In a rematch of the 1910 Series, the A’s again took down the Cubs in five games to end the Twenties.
1932 World Series – New York Yankees over Chicago Cubs (4 games to 0)
The Cubs and Ruth met again, in the 1932 World Series. Once again, Ruth got the better of his Windy City opponents, this time in a sweep.
This is also the Series where Ruth allegedly “called his shot” against Cubs hurler Charlie Root in the fifth inning of Game 3.
1935 World Series – Detroit Tigers over Chicago Cubs (4 games to 2)
Chuck Klein and his Cubs teammates were back in the World Series, but they couldn’t take care of business against Hank Greenberg, Charlie Gehringer, and company.
1938 World Series – New York Yankees over Chicago Cubs (4 games to 0)
Another Yanks-Cubs matchup, another New York sweep. This was Lou Gehrig‘s last World Series, and Joe DiMaggio’s third.
1945 World Series – Detroit Tigers over Chicago Cubs (4 games to 3)
Yet another Tigers-Cubs matchup in the World Series, this one went down to the wire. Hal Newhouser pitched on two days’ rest to win Game 7, striking out ten Cubs in nine innings while surrendering three runs.
2016 World Series – Chicago Cubs over Cleveland Indians (4 games to 3)
After a 71-year absence from the World Series, and with 108 long years having passed since their last championships, the Cubs finally got their title. It was about as tight and thrilling as a Series could have been, too, with Chicago winning Game 7 in ten innings over the Indians … who remain winless in the Series since 1948.