| 4. Round | 14/06/2009 | D.C. United | - | Chicago Fire | 2:1 | ||||
| 6. Round | 16/08/2009 | Kansas City Wizards | - | Chicago Fire | 0:2 | ||||
| 6. Round | 20/08/2009 | Chicago Fire | - | Los Angeles Galaxy | 0:2 | ||||
| 6. Round | 23/08/2009 | Chicago Fire | - | Colorado Rapids | 3:2 | ||||
| 6. Round | 30/08/2009 | Chicago Fire | - | D.C. United | 0:1 | ||||
| 7. Round | 27/09/2009 | Chicago Fire | - | Toronto FC | 2:2 | ||||
| 8. Round | 03/10/2009 | Los Angeles Galaxy | - | Chicago Fire | 1:0 |
Bulgaria