| 3. Round | 22/08/2020 | FC Cincinnati | - | D.C. United | 0:0 | ||||
| 3. Round | 30/08/2020 | Philadelphia Union | - | D.C. United | 4:1 | ||||
| 4. Round | 03/09/2020 | New York RB | - | D.C. United | 0:1 | ||||
| 4. Round | 20/09/2020 | D.C. United | - | Toronto FC | 2:2 |  |
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| 4. Round | 24/09/2020 | Nashville SC | - | D.C. United | 1:0 | ||||
| 4. Round | 28/09/2020 | D.C. United | - | New England Revolution | 0:2 | ||||
| 5. Round | 04/10/2020 | D.C. United | - | Atlanta United FC | 0:4 | ||||
| 5. Round | 08/10/2020 | New York City FC | - | D.C. United | 4:1 | ||||
| 5. Round | 12/10/2020 | Chicago Fire | - | D.C. United | 2:1 | ||||
| 5. Round | 15/10/2020 | D.C. United | - | Philadelphia Union | 2:2 | ||||
| 6. Round | 02/11/2020 | New England Revolution | - | D.C. United | 4:3 | |
USA