| 4. Round | 15/06/2008 | FC Dallas | - | Chicago Fire | 1:0 | ||||
| 4. Round | 20/06/2008 | CD Chivas | - | Chicago Fire | 2:0 | ||||
| 5. Round | 13/07/2008 | Chicago Fire | - | Toronto FC | 2:1 |
| 4. Round | 15/06/2008 | FC Dallas | - | Chicago Fire | 1:0 | ||||
| 4. Round | 20/06/2008 | CD Chivas | - | Chicago Fire | 2:0 | ||||
| 5. Round | 13/07/2008 | Chicago Fire | - | Toronto FC | 2:1 |
| Charles Brown | |
| Born: | 15.06.1975 |
| Place of birth: |
Eugene, OR, 
USA |
| Nationality: |
USA
|
| Height: | 183 cm |
| Weight: | 84 kg |
| Position(s): | Centre Back |
| Foot: | right |