| 4. Round | 23/06/2019 | Saint Louis FC | - | North Carolina FC | 2:2 | ||||
| 4. Round | 30/06/2019 | Swope Park Rangers | - | Saint Louis FC | 2:1 | ||||
| 5. Round | 21/07/2019 | Tampa Bay Rowdies | - | Saint Louis FC | 4:1 | ||||
| 5. Round | 28/07/2019 | Saint Louis FC | - | Bethlehem Steel FC | 3:0 | ||||
| 6. Round | 03/08/2019 | New York RB II | - | Saint Louis FC | 2:0 | ||||
| 6. Round | 07/08/2019 | Saint Louis FC | - | Memphis 901 | 0:0 | ||||
| 6. Round | 11/08/2019 | Saint Louis FC | - | Charleston Battery | 1:1 | ||||
| 6. Round | 18/08/2019 | Indy Eleven | - | Saint Louis FC | 2:1 | ||||
| 6. Round | 24/08/2019 | Ottawa Fury | - | Saint Louis FC | 2:1 | ||||
| 7. Round | 02/09/2019 | Saint Louis FC | - | Hartford Athletic | 3:2 | ||||
| 7. Round | 05/09/2019 | Saint Louis FC | - | Ottawa Fury | 1:0 | ||||
| 7. Round | 14/09/2019 | Birmingham Legion | - | Saint Louis FC | 0:2 | ||||
| 7. Round | 19/09/2019 | Saint Louis FC | - | New York RB II | 2:0 | ||||
| 7. Round | 29/09/2019 | Saint Louis FC | - | Atlanta United II | 1:1 | ||||
| 8. Round | 06/10/2019 | Saint Louis FC | - | Louisville City FC | 0:1 | ||||
| 8. Round | 10/10/2019 | Loudoun United | - | Saint Louis FC | 4:3 | ||||
| 8. Round | 20/10/2019 | North Carolina FC | - | Saint Louis FC | 1:0 |
Mexico