| 2. Round | 18/07/2020 | New York RB II | - | Hartford Athletic | 0:1 |  |
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| 2. Round | 21/07/2020 | Hartford Athletic | - | Loudoun United | 3:1 | ||||
| 2. Round | 26/07/2020 | Hartford Athletic | - | Philadelphia Union 2 | 3:2 | |
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| 2. Round | 30/07/2020 | Indy Eleven | - | Hartford Athletic | 4:1 | ||||
| 3. Round | 03/08/2020 | Hartford Athletic | - | Loudoun United | 4:1 | |
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| 3. Round | 29/08/2020 | Hartford Athletic | - | Pittsburgh Riverhounds | 0:3 | ||||
| 4. Round | 06/09/2020 | Hartford Athletic | - | Loudoun United | 2:1 |  |
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| 4. Round | 13/09/2020 | Pittsburgh Riverhounds | - | Hartford Athletic | 5:0 | ||||
| 4. Round | 17/09/2020 | Hartford Athletic | - | New York RB II | 3:1 | ||||
| 4. Round | 20/09/2020 | Hartford Athletic | - | Philadelphia Union 2 | 3:0 | ||||
| 4. Round | 27/09/2020 | Pittsburgh Riverhounds | - | Hartford Athletic | 0:1 | |
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| 5. Round | 05/10/2020 | New York RB II | - | Hartford Athletic | 0:2 |
Mexico