1. Round | 19/03/1999 | Tampa Bay Mutiny | - | D.C. United | 2:5 | ||||
2. Round | 02/04/1999 | MetroStars | - | D.C. United | 0:1 | ||||
2. Round | 09/04/1999 | New England Revolution | - | D.C. United | n.P. | ||||
2. Round | 16/04/1999 | D.C. United | - | San Jose Clash | n.P. | ||||
2. Round | 23/04/1999 | D.C. United | - | New England Revolution | 2:3 | ||||
3. Round | 30/04/1999 | Chicago Fire | - | D.C. United | 3:2 | ||||
3. Round | 28/05/1999 | D.C. United | - | Chicago Fire | 3:1 | ||||
4. Round | 04/06/1999 | D.C. United | - | Columbus Crew | 1:0 | ||||
4. Round | 09/06/1999 | D.C. United | - | Miami Fusion | 3:1 | ||||
4. Round | 12/06/1999 | Columbus Crew | - | D.C. United | 1:2 | ||||
4. Round | 15/06/1999 | Dallas Burn | - | D.C. United | 3:0 | ||||
4. Round | 18/06/1999 | D.C. United | - | Los Angeles Galaxy | 1:2 | ||||
4. Round | 25/06/1999 | D.C. United | - | Kansas City Wizards | 3:0 | ||||
5. Round | 03/07/1999 | San Jose Clash | - | D.C. United | n.P. | ||||
5. Round | 06/07/1999 | Columbus Crew | - | D.C. United | n.P. | ||||
5. Round | 09/07/1999 | D.C. United | - | Colorado Rapids | 1:2 |