| 4. Jornada | 19.06.1999 | Chicago Fire | - | San Jose Clash | 2:0 | ||||
| 5. Jornada | 31.07.1999 | Chicago Fire | - | Los Angeles Galaxy | 0:1 | ||||
| 6. Jornada | 05.08.1999 | Kansas City Wizards | - | Chicago Fire | 1:2 | ||||
| 6. Jornada | 25.08.1999 | Chicago Fire | - | Kansas City Wizards | 2:0 | ||||
| 6. Jornada | 28.08.1999 | Chicago Fire | - | New England Revolution | 2:1 | ||||
| 7. Jornada | 05.09.1999 | MetroStars | - | Chicago Fire | 1:2 | ||||
| 7. Jornada | 11.09.1999 | Los Angeles Galaxy | - | Chicago Fire | 1:0 | ||||
| 7. Jornada | 17.09.1999 | Chicago Fire | - | Tampa Bay Mutiny | n.P. | ||||
| 7. Jornada | 26.09.1999 | San Jose Clash | - | Chicago Fire | 2:0 |
Estados Unidos