| 4. Round | 13/07/2003 | Chicago Fire | - | D.C. United | 1:2 | ||||
| 4. Round | 20/07/2003 | Chicago Fire | - | New England Revolution | 3:1 |  |
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| 5. Round | 30/08/2003 | New England Revolution | - | Chicago Fire | 5:1 | ||||
| 7. Round | 19/10/2003 | Chicago Fire | - | Colorado Rapids | 4:3 | ||||
| 7. Round | 26/10/2003 | Columbus Crew | - | Chicago Fire | 6:2 |  |
Botswana