| 1. Round | 10/03/2019 | Charleston Battery | - | Ottawa Fury | 1:1 | ||||
| 1. Round | 17/03/2019 | Birmingham Legion | - | Ottawa Fury | 0:1 | ||||
| 2. Round | 06/04/2019 | Ottawa Fury | - | Nashville SC | 0:3 | ||||
| 2. Round | 13/04/2019 | Ottawa Fury | - | Loudoun United | 2:0 | ||||
| 3. Round | 08/05/2019 | Ottawa Fury | - | New York RB II | 1:1 | ||||
| 4. Round | 23/06/2019 | Nashville SC | - | Ottawa Fury | 3:3 | ||||
| 4. Round | 27/06/2019 | Ottawa Fury | - | Charleston Battery | 3:2 | ||||
| 4. Round | 30/06/2019 | Tampa Bay Rowdies | - | Ottawa Fury | 2:1 | ||||
| 5. Round | 06/07/2019 | New York RB II | - | Ottawa Fury | 1:1 | ||||
| 5. Round | 28/07/2019 | Memphis 901 | - | Ottawa Fury | 2:0 | ||||
| 6. Round | 31/08/2019 | Ottawa Fury | - | Pittsburgh Riverhounds | 0:4 | ||||
| 7. Round | 08/09/2019 | Atlanta United II | - | Ottawa Fury | 3:2 | ||||
| 7. Round | 19/09/2019 | Ottawa Fury | - | Tampa Bay Rowdies | 1:0 | ||||
| 7. Round | 22/09/2019 | Ottawa Fury | - | Hartford Athletic | 4:1 | ||||
| 8. Round | 03/10/2019 | Ottawa Fury | - | Indy Eleven | 1:0 | ||||
| 8. Round | 12/10/2019 | Ottawa Fury | - | Bethlehem Steel FC | 1:1 | ||||
| 8. Round | 20/10/2019 | Charlotte Independence | - | Ottawa Fury | 3:1 |
Canada
Jamaica