| 3. Round | 04/06/2005 | Chicago Fire | - | CD Chivas | 5:2 | ||||
| 3. Round | 13/06/2005 | Chicago Fire | - | FC Dallas | 2:0 | ||||
| 3. Round | 16/06/2005 | D.C. United | - | Chicago Fire | 4:3 | ||||
| 3. Round | 30/06/2005 | Chicago Fire | - | D.C. United | 4:3 | ||||
| 4. Round | 03/07/2005 | CD Chivas | - | Chicago Fire | 0:1 | ||||
| 4. Round | 10/07/2005 | Chicago Fire | - | New England Revolution | 1:0 | ||||
| 4. Round | 16/07/2005 | Chicago Fire | - | Columbus Crew | 1:1 | ||||
| 4. Round | 24/07/2005 | Colorado Rapids | - | Chicago Fire | 4:1 |
USA