| 1. Round | 22/03/2009 | Los Angeles Galaxy | - | D.C. United | 2:2 | ||||
| 2. Round | 11/04/2009 | Real Salt Lake | - | D.C. United | 2:1 |  |
|||
| 3. Round | 10/05/2009 | D.C. United | - | Toronto FC | 3:3 | ||||
| 3. Round | 31/05/2009 | New England Revolution | - | D.C. United | 2:1 | |
|||
| 4. Round | 05/06/2009 | D.C. United | - | New York RB | 2:0 | ||||
| 4. Round | 21/06/2009 | Colorado Rapids | - | D.C. United | 3:0 | ||||
| 5. Round | 19/07/2009 | D.C. United | - | Colorado Rapids | 3:1 | ||||
| 5. Round | 26/07/2009 | San Jose Earthquakes | - | D.C. United | 2:2 | ||||
| 7. Round | 06/09/2009 | FC Dallas | - | D.C. United | 2:2 | |
|||
| 6. Round | 10/09/2009 | D.C. United | - | Kansas City Wizards | 1:0 | ||||
| 8. Round | 18/10/2009 | D.C. United | - | Columbus Crew | 1:0 | |
USA