| 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 | ||||
| 4. Round | 02/06/2019 | Louisville City FC | - | Charleston Battery | 4:1 | ||||
| 4. Round | 09/06/2019 | Louisville City FC | - | Loudoun United | 2:1 | ||||
| 4. Round | 16/06/2019 | New York RB II | - | Louisville City FC | 1:0 |  |
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| 4. Round | 23/06/2019 | Louisville City FC | - | Charlotte Independence | 1:1 | ||||
| 4. Round | 30/06/2019 | Indy Eleven | - | Louisville City FC | 1:1 |  |
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| 5. Round | 07/07/2019 | Louisville City FC | - | Nashville SC | 2:1 | ||||
| 7. Round | 22/09/2019 | Louisville City FC | - | New York RB II | 5:3 | ||||
| 8. Round | 06/10/2019 | Saint Louis FC | - | Louisville City FC | 0:1 | ||||
| 8. Round | 09/10/2019 | Nashville SC | - | Louisville City FC | 2:1 | ||||
| 8. Round | 13/10/2019 | Louisville City FC | - | Swope Park Rangers | 8:3 | |
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| 8. Round | 20/10/2019 | Memphis 901 | - | Louisville City FC | 1:2 |
USA