| Boston Red Sox Postseason History |
| Year |
Opponent |
Round |
Result |
| 1999 |
New York Yankees |
ALCS |
Lost, 1-4 |
| 1999 |
Cleveland Indians |
Division Series |
Won, 3-2 |
| 1998 |
Cleveland Indians |
Division Series |
Lost, 1-3 |
| 1995 |
Cleveland Indians |
Division Series |
Lost, 0-3 |
| 1990 |
Oakland Athletics |
ALCS |
Lost, 0-4 |
| 1988 |
Oakland Athletics |
ALCS |
Lost, 0-4 |
| 1986 |
New York Mets |
World Series |
Lost, 3-4 |
| 1986 |
California Angels |
ALCS |
Won, 4-3 |
| 1975 |
Cincinnati Reds |
World Series |
Lost, 3-4 |
| 1975 |
Oakland Athletics |
ALCS |
Won, 3-0 |
| 1967 |
St. Louis Cardinals |
World Series |
Lost, 3-4 |
| 1946 |
St. Louis Cardinals |
World Series |
Lost, 3-4 |
| 1918 |
Chicago Cubs |
World Series |
Won, 4-2 |
| 1916 |
Brooklyn Dodgers |
World Series |
Won, 4-1 |
| 1915 |
Philadelphia Phillies |
World Series |
Won, 4-1 |
| 1912 |
New York Giants |
World Series |
Won, 4-3 |
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