1. Round | 19/03/1999 | Miami Fusion | - | MetroStars | n.P. | ||||
4. Round | 25/06/1999 | Columbus Crew | - | MetroStars | 2:1 | ||||
4. Round | 29/06/1999 | MetroStars | - | Tampa Bay Mutiny | n.P. | ||||
5. Round | 03/07/1999 | New England Revolution | - | MetroStars | 3:2 | ||||
5. Round | 09/07/1999 | Chicago Fire | - | MetroStars | 2:0 |