| 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 |  |
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| 7. Round | 08/09/2019 | Saint Louis FC | - | Nashville SC | 1:0 | ||||
| 7. Round | 14/09/2019 | Birmingham Legion | - | Saint Louis FC | 0:2 | |
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| 7. Round | 19/09/2019 | Saint Louis FC | - | New York RB II | 2:0 | |
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| 7. Round | 22/09/2019 | Memphis 901 | - | Saint Louis FC | 1:0 | ||||
| 7. Round | 29/09/2019 | Saint Louis FC | - | Atlanta United II | 1:1 | |
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| 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 | |
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| 8. Round | 13/10/2019 | Saint Louis FC | - | Pittsburgh Riverhounds | 0:1 | ||||
| 8. Round | 20/10/2019 | North Carolina FC | - | Saint Louis FC | 1:0 |
England