| 1. Round | 07/03/2020 | North Carolina FC | - | Louisville City FC | 0:1 | ||||
| 2. Round | 12/07/2020 | Louisville City FC | - | Pittsburgh Riverhounds | 1:3 | ||||
| 2. Round | 26/07/2020 | Louisville City FC | - | Sporting Kansas City 2 | 1:0 | ||||
| 2. Round | 30/07/2020 | Louisville City FC | - | Sporting Kansas City 2 | 1:2 | ||||
| 3. Round | 09/08/2020 | Louisville City FC | - | Indy Eleven | 1:1 | ||||
| 3. Round | 16/08/2020 | Louisville City FC | - | Loudoun United | 2:0 | ||||
| 3. Round | 20/08/2020 | Louisville City FC | - | Sporting Kansas City 2 | 4:1 | ||||
| 3. Round | 27/08/2020 | Louisville City FC | - | Indy Eleven | 1:0 | ||||
| 3. Round | 30/08/2020 | Saint Louis FC | - | Louisville City FC | 1:1 | ||||
| 4. Round | 06/09/2020 | Indy Eleven | - | Louisville City FC | 1:3 | ||||
| 4. Round | 13/09/2020 | Louisville City FC | - | Saint Louis FC | 3:0 | ||||
| 4. Round | 17/09/2020 | Indy Eleven | - | Louisville City FC | 0:2 | ||||
| 4. Round | 20/09/2020 | Louisville City FC | - | Memphis 901 | 4:1 | ||||
| 4. Round | 27/09/2020 | Saint Louis FC | - | Louisville City FC | 0:1 | ||||
| 5. Round | 04/10/2020 | Louisville City FC | - | Sporting Kansas City 2 | 2:1 |
Germany