1. Round | 09/03/2019 | North Carolina FC | - | Louisville City FC | 4:1 | ||||
1. Round | 15/03/2019 | Atlanta United II | - | Louisville City FC | 0:1 | ||||
2. Round | 14/04/2019 | Tampa Bay Rowdies | - | Louisville City FC | 1:1 | ||||
3. Round | 26/05/2019 | Bethlehem Steel FC | - | Louisville City FC | 2:2 | ||||
4. Round | 09/06/2019 | Louisville City FC | - | Loudoun United | 2:1 | ||||
4. Round | 23/06/2019 | Louisville City FC | - | Charlotte Independence | 1:1 | ||||
5. Round | 07/07/2019 | Louisville City FC | - | Nashville SC | 2:1 | ||||
5. Round | 14/07/2019 | Ottawa Fury | - | Louisville City FC | 1:1 | ||||
5. Round | 21/07/2019 | Louisville City FC | - | Bethlehem Steel FC | 0:1 | ||||
6. Round | 11/08/2019 | Louisville City FC | - | Atlanta United II | 5:1 | ||||
6. Round | 18/08/2019 | Charleston Battery | - | Louisville City FC | 1:2 |