5. Round | 22/07/1999 | Chicago Fire | - | San Jose Clash | n.P. | ||||
6. Round | 07/08/1999 | Chicago Fire | - | Colorado Rapids | 5:0 | ||||
6. Round | 13/08/1999 | Chicago Fire | - | Miami Fusion | n.P. | ||||
6. Round | 21/08/1999 | Dallas Burn | - | Chicago Fire | n.P. | ||||
6. Round | 24/08/1999 | Chicago Fire | - | Kansas City Wizards | 2:0 | ||||
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 | ||||
8. Round | 09/10/1999 | Columbus Crew | - | Chicago Fire | n.P. |