| 6. Jornada | 17.08.2008 | Chicago Fire | - | D.C. United | 0:1 | ||||
| 6. Jornada | 22.08.2008 | Los Angeles Galaxy | - | Chicago Fire | 0:1 | ||||
| 7. Jornada | 01.09.2008 | Houston Dynamo | - | Chicago Fire | 2:1 |  |
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| 7. Jornada | 07.09.2008 | Chicago Fire | - | New York RB | 1:0 | ||||
| 7. Jornada | 14.09.2008 | Colorado Rapids | - | Chicago Fire | 2:0 | ||||
| 7. Jornada | 21.09.2008 | Chicago Fire | - | FC Dallas | 1:4 | |
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| 7. Jornada | 26.09.2008 | Chicago Fire | - | Los Angeles Galaxy | 3:1 | ||||
| 8. Jornada | 05.10.2008 | Kansas City Wizards | - | Chicago Fire | 1:1 | ||||
| 8. Jornada | 12.10.2008 | Chicago Fire | - | Columbus Crew | 2:2 | |
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| 8. Jornada | 18.10.2008 | Toronto FC | - | Chicago Fire | 3:2 | ||||
| 8. Jornada | 24.10.2008 | Chicago Fire | - | New York RB | 5:2 | |
Estados Unidos