1. Round | 09/03/2019 | North Carolina FC | - | Louisville City FC | 4:1 | ||||
1. Round | 23/03/2019 | Louisville City FC | - | Hartford Athletic | 2:1 | ||||
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 | ||||
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 | ||||
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 | ||||
4. Round | 23/06/2019 | Louisville City FC | - | Charlotte Independence | 1:1 |