| 1. Round | 10/03/2019 | Charleston Battery | - | Ottawa Fury | 1:1 | ||||
| 2. Round | 28/04/2019 | Ottawa Fury | - | Atlanta United II | 2:0 | ||||
| 3. Round | 08/05/2019 | Ottawa Fury | - | New York RB II | 1:1 | ||||
| 3. Round | 12/05/2019 | Ottawa Fury | - | North Carolina FC | 2:1 | ||||
| 3. Round | 19/05/2019 | Bethlehem Steel FC | - | Ottawa Fury | 0:3 | ||||
| 3. Round | 26/05/2019 | Hartford Athletic | - | Ottawa Fury | 1:1 | ||||
| 4. Round | 02/06/2019 | Ottawa Fury | - | Charlotte Independence | 4:1 |  |
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| 4. Round | 09/06/2019 | Pittsburgh Riverhounds | - | Ottawa Fury | 2:2 | ||||
| 4. Round | 16/06/2019 | Ottawa Fury | - | Memphis 901 | 0:0 | |
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| 4. Round | 23/06/2019 | Nashville SC | - | Ottawa Fury | 3:3 | ||||
| 5. Round | 06/07/2019 | New York RB II | - | Ottawa Fury | 1:1 | ||||
| 5. Round | 14/07/2019 | Ottawa Fury | - | Louisville City FC | 1:1 | ||||
| 5. Round | 21/07/2019 | Ottawa Fury | - | Swope Park Rangers | 4:0 | ||||
| 8. Round | 03/10/2019 | Ottawa Fury | - | Indy Eleven | 1:0 | |
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| 8. Round | 09/10/2019 | Swope Park Rangers | - | Ottawa Fury | 1:2 | ||||
| 8. Round | 12/10/2019 | Ottawa Fury | - | Bethlehem Steel FC | 1:1 | ||||
| 8. Round | 20/10/2019 | Charlotte Independence | - | Ottawa Fury | 3:1 | |
Canada
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