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| 1st(1st leg) | Vaughan Azzurri | - | HFX Wanderers | 2:3 | ||
| 2nd (2nd leg) | HFX Wanderers | - | Vaughan Azzurri | 0:1 | ||
| 1st(1st leg): 16/05/2019 00:00 | 2nd (2nd leg): 22/05/2019 22:00 | Winner: HFX Wanderers | ||||
| 1st(1st leg) | AS Blainville | - | York9 FC | 0:0 | ||
| 2nd (2nd leg) | York9 FC | - | AS Blainville | 1:0 | ||
| 1st(1st leg): 16/05/2019 00:00 | 2nd (2nd leg): 23/05/2019 00:00 | Winner: York9 FC | ||||
| 1st(1st leg) | Pacific FC | - | Cavalry FC | 0:2 | ||
| 2nd (2nd leg) | Cavalry FC | - | Pacific FC | 2:1 | ||
| 1st(1st leg): 16/05/2019 03:30 | 2nd (2nd leg): 23/05/2019 02:30 | Winner: Cavalry FC | ||||
