| 3. Round | 09/08/2020 | Louisville City FC | - | Indy Eleven | 1:1 | ||||
| 3. Round | 16/08/2020 | Louisville City FC | - | Loudoun United | 2:0 | ||||
| 4. Round | 13/09/2020 | Louisville City FC | - | Saint Louis FC | 3:0 |  |
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| 4. Round | 17/09/2020 | Indy Eleven | - | Louisville City FC | 0:2 | ||||
| 4. Round | 20/09/2020 | Louisville City FC | - | Memphis 901 | 4:1 | ||||
| 5. Round | 04/10/2020 | Louisville City FC | - | Sporting Kansas City 2 | 2:1 |
Jamaica