| 2. Round | 12/04/2008 | San Jose Earthquakes | - | Chicago Fire | 0:1 | ||||
| 4. Round | 08/06/2008 | Chicago Fire | - | D.C. United | 1:2 | ||||
| 6. Round | 22/08/2008 | Los Angeles Galaxy | - | Chicago Fire | 0:1 | ||||
| 8. Round | 05/10/2008 | Kansas City Wizards | - | Chicago Fire | 1:1 | ||||
| 8. Round | 12/10/2008 | Chicago Fire | - | Columbus Crew | 2:2 |
USA