| 1. Round | 09/03/2014 | D.C. United | - | Columbus Crew | 0:3 | ||||
| 1. Round | 22/03/2014 | Toronto FC | - | D.C. United | 1:0 | ||||
| 1. Round | 29/03/2014 | D.C. United | - | Chicago Fire | 2:2 | ||||
| 2. Round | 06/04/2014 | D.C. United | - | New England Revolution | 2:0 |  |
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| 2. Round | 13/04/2014 | D.C. United | - | New York RB | 1:0 | ||||
| 2. Round | 20/04/2014 | Columbus Crew | - | D.C. United | 1:1 | ||||
| 2. Round | 27/04/2014 | D.C. United | - | FC Dallas | 4:1 | ||||
| 3. Round | 04/05/2014 | Portland Timbers | - | D.C. United | 3:2 | ||||
| 3. Round | 10/05/2014 | Philadelphia Union | - | D.C. United | 0:1 | ||||
| 3. Round | 18/05/2014 | D.C. United | - | Impact de Montréal | 1:1 | ||||
| 3. Round | 22/05/2014 | D.C. United | - | Houston Dynamo | 2:0 | ||||
| 4. Round | 07/06/2014 | D.C. United | - | Columbus Crew | 0:0 | ||||
| 4. Round | 12/06/2014 | Impact de Montréal | - | D.C. United | 2:4 | ||||
| 5. Round | 06/07/2014 | Toronto FC | - | D.C. United | 1:2 | ||||
| 5. Round | 12/07/2014 | San Jose Earthquakes | - | D.C. United | 1:2 | ||||
| 5. Round | 21/07/2014 | D.C. United | - | CD Chivas | 3:1 | |
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| 5. Round | 31/07/2014 | D.C. United | - | Toronto FC | 3:0 |
USA
Ireland