| 3. Jornada | 07.05.2009 | Kansas City Wizards | - | D.C. United | 1:1 |  |
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| 4. Jornada | 14.06.2009 | D.C. United | - | Chicago Fire | 2:1 | ||||
| 4. Jornada | 21.06.2009 | Colorado Rapids | - | D.C. United | 3:0 | |
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| 6. Jornada | 02.08.2009 | Houston Dynamo | - | D.C. United | 4:3 | ||||
| 6. Jornada | 10.09.2009 | D.C. United | - | Kansas City Wizards | 1:0 | |
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| 7. Jornada | 13.09.2009 | D.C. United | - | Seattle Sounders | 1:2 | |
Trinidad y Tobago