4. Round | 15/06/2008 | FC Dallas | - | Chicago Fire | 1:0 | ||||
4. Round | 20/06/2008 | CD Chivas | - | Chicago Fire | 2:0 | ||||
5. Round | 20/07/2008 | Chicago Fire | - | Real Salt Lake | 0:0 | ||||
5. Round | 28/07/2008 | Kansas City Wizards | - | Chicago Fire | 0:0 | ||||
6. Round | 03/08/2008 | Chicago Fire | - | CD Chivas | 1:0 | ||||
6. Round | 17/08/2008 | Chicago Fire | - | D.C. United | 0:1 | ||||
6. Round | 22/08/2008 | Los Angeles Galaxy | - | Chicago Fire | 0:1 | ||||
8. Round | 12/10/2008 | Chicago Fire | - | Columbus Crew | 2:2 | ||||
8. Round | 24/10/2008 | Chicago Fire | - | New York RB | 5:2 |