2. Round | 12/07/2020 | Louisville City FC | - | Pittsburgh Riverhounds | 1:3 | ||||
2. Round | 19/07/2020 | Louisville City FC | - | Saint Louis FC | 0:1 | ||||
2. Round | 30/07/2020 | Louisville City FC | - | Sporting Kansas City 2 | 1:2 | ||||
3. Round | 16/08/2020 | Louisville City FC | - | Loudoun United | 2:0 | ||||
3. Round | 30/08/2020 | Saint Louis FC | - | Louisville City FC | 1:1 | ||||
4. Round | 27/09/2020 | Saint Louis FC | - | Louisville City FC | 0:1 |