| 5. Jornada | 13.07.2008 | Chicago Fire | - | Toronto FC | 2:1 | ||||
| 5. Jornada | 20.07.2008 | Chicago Fire | - | Real Salt Lake | 0:0 | ||||
| 6. Jornada | 03.08.2008 | Chicago Fire | - | CD Chivas | 1:0 | ||||
| 6. Jornada | 10.08.2008 | New England Revolution | - | Chicago Fire | 1:2 | ||||
| 7. Jornada | 01.09.2008 | Houston Dynamo | - | Chicago Fire | 2:1 | ||||
| 7. Jornada | 07.09.2008 | Chicago Fire | - | New York RB | 1:0 | ||||
| 7. Jornada | 21.09.2008 | Chicago Fire | - | FC Dallas | 1:4 | ||||
| 7. Jornada | 26.09.2008 | Chicago Fire | - | Los Angeles Galaxy | 3:1 | ||||
| 8. Jornada | 12.10.2008 | Chicago Fire | - | Columbus Crew | 2:2 | ||||
| 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