2. Round | 31/03/2000 | Columbus Crew | - | Chicago Fire | 0:2 | ||||
2. Round | 07/04/2000 | D.C. United | - | Chicago Fire | 3:2 | ||||
2. Round | 27/04/2000 | Chicago Fire | - | Tampa Bay Mutiny | 5:1 | ||||
3. Round | 02/05/2000 | Chicago Fire | - | Colorado Rapids | 1:2 | ||||
4. Round | 09/06/2000 | Miami Fusion | - | Chicago Fire | 4:2 |