| Chicago Cubs Postseason History |
| Year |
Opponent |
Round |
Result |
| 1998 |
Atlanta Braves |
Division Series |
Lost, 0-3 |
| 1989 |
San Francisco Giants |
NLCS |
Lost, 1-4 |
| 1984 |
San Diego Padres |
NLCS |
Lost, 2-3 |
| 1945 |
Detroit Tigers |
World Series |
Lost, 3-4 |
| 1938 |
New York Yankees |
World Series |
Lost, 0-4 |
| 1935 |
Detroit Tigers |
World Series |
Lost, 2-4 |
| 1932 |
New York Yankees |
World Series |
Lost, 0-4 |
| 1929 |
Philadelphia A's |
World Series |
Lost, 1-4 |
| 1918 |
Boston Red Sox |
World Series |
Lost, 2-4 |
| 1910 |
Philadelphia A's |
World Series |
Lost, 1-4 |
| 1908 |
Detroit Tigers |
World Series |
Won, 4-1 |
| 1907 |
Detroit Tigers |
World Series |
Won, 4-0 |
| 1906 |
Chicago White Sox |
World Series |
Lost, 2-4 |
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