| 1. Jornada | 16.03.2019 | Atlanta United II | - | Louisville City FC | 0:1 | ||||
| 1. Jornada | 31.03.2019 | Louisville City FC | - | Birmingham Legion | 2:3 | ||||
| 2. Jornada | 07.04.2019 | Louisville City FC | - | Pittsburgh Riverhounds | 0:1 | ||||
| 2. Jornada | 14.04.2019 | Tampa Bay Rowdies | - | Louisville City FC | 1:1 | ||||
| 2. Jornada | 21.04.2019 | Louisville City FC | - | Ottawa Fury | 1:0 | ||||
| 3. Jornada | 01.05.2019 | Louisville City FC | - | Memphis 901 | 2:1 | ||||
| 3. Jornada | 07.05.2019 | Swope Park Rangers | - | Louisville City FC | 3:2 | ||||
| 3. Jornada | 12.05.2019 | Birmingham Legion | - | Louisville City FC | 0:3 | ||||
| 3. Jornada | 19.05.2019 | Louisville City FC | - | Saint Louis FC | 0:0 |  |
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| 3. Jornada | 26.05.2019 | Bethlehem Steel FC | - | Louisville City FC | 2:2 | ||||
| 4. Jornada | 02.06.2019 | Louisville City FC | - | Charleston Battery | 4:1 | ||||
| 5. Jornada | 14.07.2019 | Ottawa Fury | - | Louisville City FC | 1:1 | ||||
| 5. Jornada | 29.07.2019 | Loudoun United | - | Louisville City FC | 3:0 | ||||
| 7. Jornada | 29.09.2019 | Louisville City FC | - | Tampa Bay Rowdies | 2:2 | ||||
| 8. Jornada | 09.10.2019 | Nashville SC | - | Louisville City FC | 2:1 |
Jamaica