6. Round | 03/08/2008 | Chicago Fire | - | CD Chivas | 1:0 | ||||
6. Round | 10/08/2008 | New England Revolution | - | Chicago Fire | 1:2 | ||||
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 |