| 3. Round | 05/05/2000 | Colorado Rapids | - | D.C. United | 2:5 | ||||
| 4. Round | 02/06/2000 | Columbus Crew | - | D.C. United | 1:1 aet | ||||
| 4. Round | 09/06/2000 | D.C. United | - | Kansas City Wizards | 0:0 | ||||
| 4. Round | 16/06/2000 | Chicago Fire | - | D.C. United | 3:2 | ||||
| 4. Round | 20/06/2000 | MetroStars | - | D.C. United | 2:2 aet | ||||
| 4. Round | 23/06/2000 | D.C. United | - | Dallas Burn | 2:0 | ||||
| 4. Round | 27/06/2000 | D.C. United | - | Los Angeles Galaxy | 1:2 | ||||
| 5. Round | 30/06/2000 | D.C. United | - | Colorado Rapids | 1:1 aet | ||||
| 5. Round | 07/07/2000 | Dallas Burn | - | D.C. United | 3:0 | ||||
| 5. Round | 11/07/2000 | D.C. United | - | Tampa Bay Mutiny | 2:2 aet |  |
|||
| 5. Round | 14/07/2000 | Los Angeles Galaxy | - | D.C. United | 1:2 | ||||
| 6. Round | 11/08/2000 | Dallas Burn | - | D.C. United | 1:0 | ||||
| 6. Round | 25/08/2000 | D.C. United | - | Miami Fusion | 2:1 aet | ||||
| 6. Round | 29/08/2000 | New England Revolution | - | D.C. United | 1:0 | ||||
| 7. Round | 02/09/2000 | D.C. United | - | New England Revolution | 2:0 | ||||
| 7. Round | 08/09/2000 | D.C. United | - | Miami Fusion | 2:6 | |
USA