PLAYOFFS: Wednesday, August 30, 2023
- #1 and #2 seed receive byes into the semi-finals
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm (quarter-final A) | Boombatz FC | 8-1 | Unity FC | OSA Grass #2 |
| 9:00pm (quarter-final B) | Piacere FC | 2-0 | CICC | OSA Grass #2 |
PLAYOFFS: Wednesday, September 6, 2023
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Rudge FC | 2-8 | Boombatz FC | OSA Grass #2 |
| 9:00pm | Toronto AFC | 4-0 | Piacere FC | OSA Grass #2 |
PLAYOFFS: Wednesday, September 13, 2023
| Kick-off | Home Team | Score | Away Team | Venue |
| 9:30pm | Toronto AFC ? | 4-4 (PK) | Boombatz FC ? | Ontario Soccer Stadium |