| 1. Round | 09/03/2019 | North Carolina FC | - | Louisville City FC | 4:1 |  |
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| 1. Round | 16/03/2019 | Bethlehem Steel FC | - | North Carolina FC | 0:1 | |
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| 1. Round | 30/03/2019 | North Carolina FC | - | Charleston Battery | 1:1 | ||||
| 2. Round | 07/04/2019 | North Carolina FC | - | Memphis 901 | 1:1 | |
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| 2. Round | 14/04/2019 | Atlanta United II | - | North Carolina FC | 2:1 | |
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| 2. Round | 21/04/2019 | Charlotte Independence | - | North Carolina FC | 0:3 | |
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| 2. Round | 28/04/2019 | North Carolina FC | - | Hartford Athletic | 4:1 | |
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| 3. Round | 05/05/2019 | Indy Eleven | - | North Carolina FC | 0:0 | ||||
| 3. Round | 12/05/2019 | Ottawa Fury | - | North Carolina FC | 2:1 | ||||
| 3. Round | 19/05/2019 | North Carolina FC | - | Birmingham Legion | 0:0 | ||||
| 3. Round | 25/05/2019 | New York RB II | - | North Carolina FC | 1:2 | ||||
| 8. Round | 13/10/2019 | Nashville SC | - | North Carolina FC | 2:0 | ||||
| 8. Round | 20/10/2019 | North Carolina FC | - | Saint Louis FC | 1:0 |
Netherlands