The draw was held on February 12, 2019.[1]
| First qualifying round May 15 & 22 | Second qualifying round June 4–5 & 11–12 | Third qualifying round July 10 & 24 | Semi-finals August 7 & 14 | Final September 18 & 25 | ||||||||||||||||||||||||
| Montreal Impact | 2 | 1 | 3 | |||||||||||||||||||||||||
| FC Edmonton | 1 | 1 | 2 | York9 | 2 | 0 | 2 | |||||||||||||||||||||
| A.S. Blainville | 0 | 0 | 0 | York9 | 3 | 0 | 3 | Montreal Impact | 2 | 1 | 3 | |||||||||||||||||
| York9 | 0 | 1 | 1 | Cavalry FC | 1 | 0 | 1 | |||||||||||||||||||||
| Vancouver Whitecaps FC | 0 | 1 | 1 | |||||||||||||||||||||||||
| Forge FC | 1 | 1 | 2 | Cavalry FC | 0 | 2 | 2 | Montreal Impact (p) | 1 | 0 | 1 (3) | |||||||||||||||||
| Pacific FC | 0 | 1 | 1 | Cavalry FC | 1 | 2 | 3 | Toronto FC | 0 | 1 | 1 (1) | |||||||||||||||||
| Cavalry FC | 2 | 2 | 4 | |||||||||||||||||||||||||
| Ottawa Fury | 0 | 0 | 0 | |||||||||||||||||||||||||
| Ottawa Fury | 3 | 2 | 5 | Toronto FC | 2 | 3 | 5 | |||||||||||||||||||||
| Valour FC | 1 | 0 | 1 | HFX Wanderers | 2 | 2 | 4 | |||||||||||||||||||||
| Vaughan Azzurri | 2 | 1 | 3 | HFX Wanderers | 2 | 2 | 4 | |||||||||||||||||||||
| HFX Wanderers (a) | 3 | 0 | 3 | |||||||||||||||||||||||||
- ^ "Canada Soccer continues to provide expanded international opportunities with two spots on the path to Scotiabank Concacaf Champions League". Canada Soccer. February 12, 2019. Retrieved February 19, 2019.