| 1. Round | 10/03/2019 | Nashville SC | - | Loudoun United | 2:0 | ||||
| 1. Round | 17/03/2019 | Nashville SC | - | Saint Louis FC | 0:1 | ||||
| 1. Round | 24/03/2019 | New York RB II | - | Nashville SC | 1:1 |  |
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| 2. Round | 06/04/2019 | Ottawa Fury | - | Nashville SC | 0:3 | ||||
| 2. Round | 14/04/2019 | Nashville SC | - | Memphis 901 | 2:0 | ||||
| 2. Round | 21/04/2019 | Charleston Battery | - | Nashville SC | 3:1 | ||||
| 2. Round | 28/04/2019 | Pittsburgh Riverhounds | - | Nashville SC | 2:2 | ||||
| 3. Round | 12/05/2019 | Nashville SC | - | Swope Park Rangers | 5:1 | ||||
| 3. Round | 19/05/2019 | Nashville SC | - | Charlotte Independence | 1:1 | ||||
| 3. Round | 26/05/2019 | Indy Eleven | - | Nashville SC | 0:0 | ||||
| 4. Round | 16/06/2019 | Hartford Athletic | - | Nashville SC | 2:3 | ||||
| 4. Round | 23/06/2019 | Nashville SC | - | Ottawa Fury | 3:3 | ||||
| 4. Round | 30/06/2019 | North Carolina FC | - | Nashville SC | 1:0 | ||||
| 5. Round | 07/07/2019 | Louisville City FC | - | Nashville SC | 2:1 | ||||
| 5. Round | 18/07/2019 | Memphis 901 | - | Nashville SC | 0:2 | |
England