1. Round | 09/03/2019 | Saint Louis FC | - | Indy Eleven | 2:1 | ||||
2. Round | 07/04/2019 | Atlanta United II | - | Saint Louis FC | 0:2 | ||||
2. Round | 14/04/2019 | Saint Louis FC | - | Birmingham Legion | 2:3 | ||||
4. Round | 09/06/2019 | Hartford Athletic | - | Saint Louis FC | 2:1 | ||||
4. Round | 16/06/2019 | Bethlehem Steel FC | - | Saint Louis FC | 3:1 | ||||
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 |