| 1. Round | 24/03/2000 | Kansas City Wizards | - | Chicago Fire | 4:3 | ||||
| 2. Round | 31/03/2000 | Columbus Crew | - | Chicago Fire | 0:2 | ||||
| 2. Round | 07/04/2000 | D.C. United | - | Chicago Fire | 3:2 | ||||
| 3. Round | 05/05/2000 | Miami Fusion | - | Chicago Fire | 0:3 | ||||
| 3. Round | 12/05/2000 | Chicago Fire | - | San Jose Earthquakes | 4:1 | ||||
| 3. Round | 26/05/2000 | MetroStars | - | Chicago Fire | 4:1 | ||||
| 4. Round | 03/06/2000 | Chicago Fire | - | Kansas City Wizards | 3:2 | ||||
| 4. Round | 06/06/2000 | Chicago Fire | - | Miami Fusion | 2:1 | ||||
| 4. Round | 09/06/2000 | Miami Fusion | - | Chicago Fire | 4:2 | ||||
| 5. Round | 20/07/2000 | Colorado Rapids | - | Chicago Fire | 1:1 aet | ||||
| 6. Round | 15/08/2000 | Dallas Burn | - | Chicago Fire | 3:0 | ||||
| 6. Round | 18/08/2000 | Chicago Fire | - | Los Angeles Galaxy | 2:1 | ||||
| 6. Round | 25/08/2000 | Tampa Bay Mutiny | - | Chicago Fire | 3:3 aet | ||||
| 7. Round | 02/09/2000 | Chicago Fire | - | Colorado Rapids | 2:1 | ||||
| 7. Round | 05/09/2000 | Chicago Fire | - | Columbus Crew | 3:1 | ||||
| 7. Round | 08/09/2000 | Columbus Crew | - | Chicago Fire | 2:3 |
USA