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| 1st(1st leg) | Forge FC | - | Cavalry FC | 1:1 | ||
| 2nd (2nd leg) | Cavalry FC | - | Forge FC | 2:1 | ||
| 1st(1st leg): 05/06/2019 00:30 | 2nd (2nd leg): 12/06/2019 02:30 | Winner: Cavalry FC | ||||
| 1st(1st leg) | HFX Wanderers | - | Valour FC | 2:1 | ||
| 2nd (2nd leg) | Valour FC | - | HFX Wanderers | 0:2 | ||
| 1st(1st leg): 05/06/2019 22:15 | 2nd (2nd leg): 13/06/2019 01:30 | Winner: HFX Wanderers | ||||
| 1st(1st leg) | York9 FC | - | FC Edmonton | 3:1 | ||
| 2nd (2nd leg) | FC Edmonton | - | York9 FC | 1:0 | ||
| 1st(1st leg): 06/06/2019 00:00 | 2nd (2nd leg): 13/06/2019 02:30 | Winner: York9 FC | ||||
