| 2. Round | 27/04/2008 | D.C. United | - | Real Salt Lake | 4:1 | ||||
| 3. Round | 04/05/2008 | Colorado Rapids | - | D.C. United | 2:0 | ||||
| 3. Round | 09/05/2008 | D.C. United | - | Chicago Fire | 0:2 | ||||
| 4. Round | 15/06/2008 | D.C. United | - | New York RB | 4:1 | ||||
| 4. Round | 24/07/2008 | D.C. United | - | Houston Dynamo | 0:2 | ||||
| 6. Round | 03/08/2008 | D.C. United | - | Kansas City Wizards | 2:0 | ||||
| 6. Round | 17/08/2008 | Chicago Fire | - | D.C. United | 0:1 | ||||
| 6. Round | 21/08/2008 | New England Revolution | - | D.C. United | 2:1 | ||||
| 6. Round | 24/08/2008 | D.C. United | - | Colorado Rapids | 3:0 |  |
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| 7. Round | 14/09/2008 | D.C. United | - | FC Dallas | 2:2 |
USA