| 1. Round | 17/03/2019 | Birmingham Legion | - | Ottawa Fury | 0:1 | ||||
| 5. Round | 06/07/2019 | New York RB II | - | Ottawa Fury | 1:1 | ||||
| 6. Round | 03/08/2019 | Ottawa Fury | - | Birmingham Legion | 0:0 | ||||
| 6. Round | 18/08/2019 | Loudoun United | - | Ottawa Fury | 1:3 | ||||
| 6. Round | 24/08/2019 | Ottawa Fury | - | Saint Louis FC | 2:1 | ||||
| 7. Round | 08/09/2019 | Atlanta United II | - | Ottawa Fury | 3:2 |  |
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| 7. Round | 12/09/2019 | Indy Eleven | - | Ottawa Fury | 2:0 | |
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| 7. Round | 19/09/2019 | Ottawa Fury | - | Tampa Bay Rowdies | 1:0 | ||||
| 7. Round | 22/09/2019 | Ottawa Fury | - | Hartford Athletic | 4:1 |
Canada