1. Round | 19/03/1999 | San Jose Clash | - | Chicago Fire | 1:3 | ||||
1. Round | 26/03/1999 | Kansas City Wizards | - | Chicago Fire | 0:3 | ||||
2. Round | 02/04/1999 | Miami Fusion | - | Chicago Fire | 1:4 | ||||
3. Round | 30/04/1999 | Chicago Fire | - | D.C. United | 3:2 | ||||
3. Round | 07/05/1999 | Tampa Bay Mutiny | - | Chicago Fire | n.P. | ||||
3. Round | 15/05/1999 | Chicago Fire | - | Colorado Rapids | 0:1 | ||||
3. Round | 28/05/1999 | D.C. United | - | Chicago Fire | 3:1 | ||||
4. Round | 11/06/1999 | Los Angeles Galaxy | - | Chicago Fire | 2:1 | ||||
5. Round | 30/07/1999 | Chicago Fire | - | Los Angeles Galaxy | 0:1 | ||||
6. Round | 27/08/1999 | Chicago Fire | - | New England Revolution | 2:1 | ||||
7. Round | 04/09/1999 | MetroStars | - | Chicago Fire | 1:2 | ||||
7. Round | 22/09/1999 | Chicago Fire | - | Columbus Crew | 1:2 | ||||
7. Round | 25/09/1999 | San Jose Clash | - | Chicago Fire | 2:0 |