| 1. Round | 10/03/2019 | Birmingham Legion | - | Bethlehem Steel FC | 0:2 | ||||
| 1. Round | 16/03/2019 | Bethlehem Steel FC | - | North Carolina FC | 0:1 | ||||
| 3. Round | 04/05/2019 | Loudoun United | - | Bethlehem Steel FC | 3:3 | ||||
| 3. Round | 12/05/2019 | Bethlehem Steel FC | - | Atlanta United II | 1:1 |  |
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| 3. Round | 19/05/2019 | Bethlehem Steel FC | - | Ottawa Fury | 0:3 | ||||
| 3. Round | 26/05/2019 | Bethlehem Steel FC | - | Louisville City FC | 2:2 |  |
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| 4. Round | 01/06/2019 | New York RB II | - | Bethlehem Steel FC | 4:0 | |
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| 5. Round | 11/07/2019 | Bethlehem Steel FC | - | New York RB II | 3:4 | ||||
| 7. Round | 01/09/2019 | Bethlehem Steel FC | - | Swope Park Rangers | 2:0 |  |
Jamaica