Wednesday, June 7, 2023 – Gameweek 1
OSA #2 (7601 Martin Grove Rd – Directly in front of the Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Piacere FC | Linuzzu FC | OSA Grass #2 | |
| 9:00pm | Boombatz FC | Rudge FC | OSA Grass #2 |
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 9:00pm | Vida FC | Leafs | Woodbridge College |
Wednesday, June 14, 2023 – Gameweek 2
OSA #2 (7601 Martin Grove Rd – Directly in front of the Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Rudge FC | Vida FC | OSA Grass #2 | |
| 9:00pm | Piacere FC | Leafs | OSA Grass #2 |
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 9:00pm | Linuzzu FC | Boombatz FC | Woodbridge College |
Wednesday, June 21, 2023 – Gameweek 3
OSA #2 (7601 Martin Grove Rd – Directly in front of the Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Linuzzu FC | Rudge FC | OSA Grass #2 | |
| 9:00pm | Boombatz FC | Leafs | OSA Grass #2 |
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 9:00pm | Piacere FC | Vida FC | Woodbridge College |