Tuesday, June 6, 2023 – Gameweek 1
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Calcio e Pepe | Bobo FC | Woodbridge College | |
| 9:00pm | Molino City | Woodford City | Woodbridge College |
OSA #2 (7601 Martin Grove Rd – Directly in front of Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Dubai Strikers | 4B Lunch FC | OSA Grass #2 | |
| 9:00pm | Dingleberries | Bluehaven City | OSA Grass #2 |
Tuesday, June 13, 2023 – Gameweek 2
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Bluehaven City | Molino City | Woodbridge College | |
| 9:00pm | Dubai Strikers | Woodford City | Woodbridge College |
OSA #2 (7601 Martin Grove Rd – Directly in front of Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Bobo FC | Dingleberries | OSA Grass #2 | |
| 9:00pm | 4B Lunch FC | Calcio e Pepe | OSA Grass #2 |
Tuesday, June 20, 2023 – Gameweek 3
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | 4B Lunch FC | Bobo FC | Woodbridge College | |
| 9:00pm | Bluehaven City | Woodford City | Woodbridge College |
OSA #2 (7601 Martin Grove Rd – Directly in front of Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Dubai Strikers | Molino City | OSA Grass #2 | |
| 9:00pm | Calcio e Pepe | Dingleberries | OSA Grass #2 |