| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 06.07.2019 | Matchday 1 | Matchday 1 | A | ![]() | Forge FC | W | 2:1 |
| 14.07.2019 | Matchday 1 | Matchday 1 | A | ![]() | Inter Toronto | L | 1:2 |
| 18.07.2019 | Matchday 1 | Matchday 1 | H | ![]() | Valour FC | D | 0:0 |
| 28.07.2019 | Matchday 1 | Matchday 1 | H | ![]() | Forge FC | D | 1:1 |
| 01.08.2019 | Matchday 1 | Matchday 1 | H | ![]() | HFX | W | 2:0 |
| 11.08.2019 | Matchday 2 | Matchday 2 | H | ![]() | Pacific FC | W | 3:1 |
| 17.08.2019 | Matchday 2 | Matchday 2 | A | ![]() | Cavalry | D | 0:0 |
| 20.08.2019 | Matchday 2 | Matchday 2 | A | ![]() | Valour FC | L | 1:3 |
| 26.08.2019 | Matchday 2 | Matchday 2 | H | ![]() | Inter Toronto | D | 2:2 |
| 02.09.2019 | Matchday 3 | Matchday 3 | A | ![]() | HFX | D | 0:0 |
| 12.09.2019 | Matchday 3 | Matchday 3 | H | ![]() | Cavalry | L | 0:1 |
| 14.09.2019 | Matchday 3 | Matchday 3 | A | ![]() | Pacific FC | L | 0:1 |
| 22.09.2019 | Matchday 3 | Matchday 3 | H | ![]() | Inter Toronto | L | 1:3 |
| 28.09.2019 | Matchday 3 | Matchday 3 | A | ![]() | HFX | D | 1:1 |
| 03.10.2019 | Matchday 4 | Matchday 4 | H | ![]() | Forge FC | L | 0:1 |
| 05.10.2019 | Matchday 4 | Matchday 4 | A | ![]() | Valour FC | L | 1:3 |
| 17.10.2019 | Matchday 4 | Matchday 4 | H | ![]() | Pacific FC | W | 3:1 |
| 19.10.2019 | Matchday 4 | Matchday 4 | A | ![]() | Cavalry | L | 1:3 |
| Date | Round | Round | H/A | Res. | |||
| 01.07.2019 | Matchday 3 | Matchday 3 | H | ![]() | HFX | W | 2:0 |
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