| 6. Round | 03/08/2008 | Chicago Fire | - | CD Chivas | 1:0 |  |
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| 6. Round | 10/08/2008 | New England Revolution | - | Chicago Fire | 1:2 | |
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| 6. Round | 17/08/2008 | Chicago Fire | - | D.C. United | 0:1 | ||||
| 7. Round | 01/09/2008 | Houston Dynamo | - | Chicago Fire | 2:1 | ||||
| 8. Round | 05/10/2008 | Kansas City Wizards | - | Chicago Fire | 1:1 | ||||
| 8. Round | 18/10/2008 | Toronto FC | - | Chicago Fire | 3:2 |
Guatemala