| 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 | ||||
| 5. Round | 28/07/2019 | Memphis 901 | - | Ottawa Fury | 2:0 | ||||
| 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 | ||||
| 6. Round | 31/08/2019 | Ottawa Fury | - | Pittsburgh Riverhounds | 0:4 | ||||
| 7. Round | 05/09/2019 | Saint Louis FC | - | Ottawa Fury | 1:0 |  |
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| 7. Round | 08/09/2019 | Atlanta United II | - | Ottawa Fury | 3:2 | ||||
| 7. Round | 12/09/2019 | Indy Eleven | - | Ottawa Fury | 2:0 | ||||
| 7. Round | 19/09/2019 | Ottawa Fury | - | Tampa Bay Rowdies | 1:0 | ||||
| 7. Round | 22/09/2019 | Ottawa Fury | - | Hartford Athletic | 4:1 | ||||
| 7. Round | 29/09/2019 | North Carolina FC | - | Ottawa Fury | 3:1 | |
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| 8. Round | 20/10/2019 | Charlotte Independence | - | Ottawa Fury | 3:1 |
Canada