Cubs Playoff Appearances
From Wiklifield
The Cubs have qualified for the postseason on 16 separate occasions. They have won 10 National League pennants(1906-1908, 1910, 1918, 1929, 1932, 1935, 1938, 1945), 3 National League Central crowns(2003, 2007 & 2008), 2 National League East titles(1984 & 1989), 1 Wild Card spot(1998) and 2 World Series championships(1907 & 1908) since 1900. They also won 6 National League pennants before 1900 (1876, 1880-1882 and 1885-1886) which was considered the baseball championship at the time. They have a lifetime 28-55-1 (.333 %) record in the postseason.
| Year | Opponents | Results |
| 2008 | Los Angeles Dodgers | Lost 3-0 in NLDS |
| 2007 | Arizona Diamondbacks | Lost 3-0 in NLDS |
| 2003 | Florida Marlins | Lost 4-3 in NLCS |
| 2003 | Atlanta Braves | Won 3-2 in NLDS |
| 1998 | Atlanta Braves | Lost 3-0 in NLDS |
| 1989 | San Francisco Giants | Lost 4-1 in NLCS |
| 1984 | San Diego Padres | Lost 3-2 in NLCS |
| 1945 | Detroit Tigers | Lost 4-3 |
| 1938 | New York Yankees | Lost 4-0 |
| 1935 | Detroit Tigers | Lost 4-2 |
| 1932 | New York Yankees | Lost 4-0 |
| 1929 | Philadelphia Athletics | Lost 4-1 |
| 1918 | Boston Red Sox | Lost 4-2 |
| 1910 | Philadelphia Athletics | Lost 4-1 |
| 1908 | Detroit Tigers | Won 4-1 |
| 1907 | Detroit Tigers | Won 4-0-1 |
| 1906 | Chicago White Sox | Lost 4-2 |
