| 3. Round | 12/06/2004 | Los Angeles Galaxy | - | Chicago Fire | 3:2 | ||||
| 3. Round | 20/06/2004 | Chicago Fire | - | San Jose Earthquakes | 1:1 | ||||
| 3. Round | 28/06/2004 | Chicago Fire | - | Los Angeles Galaxy | 0:1 | ||||
| 4. Round | 18/07/2004 | Chicago Fire | - | MetroStars | 1:1 | ||||
| 4. Round | 25/07/2004 | MetroStars | - | Chicago Fire | 2:1 | ||||
| 4. Round | 29/07/2004 | Colorado Rapids | - | Chicago Fire | 2:0 | ||||
| 5. Round | 12/08/2004 | Chicago Fire | - | San Jose Earthquakes | 2:1 | ||||
| 6. Round | 05/09/2004 | Chicago Fire | - | D.C. United | 3:1 |  |
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| 6. Round | 19/09/2004 | D.C. United | - | Chicago Fire | 3:1 | ||||
| 7. Round | 07/10/2004 | Chicago Fire | - | Columbus Crew | 0:1 |
USA