| 1. Round | 15/03/2019 | Atlanta United II | - | Louisville City FC | 0:1 | ||||
| 1. Round | 31/03/2019 | Louisville City FC | - | Birmingham Legion | 2:3 | ||||
| 2. Round | 07/04/2019 | Louisville City FC | - | Pittsburgh Riverhounds | 0:1 | ||||
| 2. Round | 14/04/2019 | Tampa Bay Rowdies | - | Louisville City FC | 1:1 | ||||
| 2. Round | 21/04/2019 | Louisville City FC | - | Ottawa Fury | 1:0 | ||||
| 3. Round | 01/05/2019 | Louisville City FC | - | Memphis 901 | 2:1 | ||||
| 3. Round | 07/05/2019 | Swope Park Rangers | - | Louisville City FC | 3:2 | ||||
| 3. Round | 12/05/2019 | Birmingham Legion | - | Louisville City FC | 0:3 | ||||
| 3. Round | 19/05/2019 | Louisville City FC | - | Saint Louis FC | 0:0 |  |
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| 3. Round | 26/05/2019 | Bethlehem Steel FC | - | Louisville City FC | 2:2 | ||||
| 4. Round | 02/06/2019 | Louisville City FC | - | Charleston Battery | 4:1 | ||||
| 5. Round | 14/07/2019 | Ottawa Fury | - | Louisville City FC | 1:1 | ||||
| 5. Round | 29/07/2019 | Loudoun United | - | Louisville City FC | 3:0 | ||||
| 7. Round | 29/09/2019 | Louisville City FC | - | Tampa Bay Rowdies | 2:2 | ||||
| 8. Round | 09/10/2019 | Nashville SC | - | Louisville City FC | 2:1 |
Jamaica