Thursday, June 8, 2023 – Gameweek 1
Ontario Soccer Stadium (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Calcio Kings | S.S. Ladzio | Ontario Soccer Stadium | |
| 9:00pm | Stugotz FC | AFC Woodbridge | Ontario Soccer Stadium |
OSA #2 (7601 Martin Grove Rd – Directly in front of the Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Crodies | Brethrenz United | OSA Grass #2 | |
| 9:00pm | Da Shmurdas | La Familia FC | OSA Grass #2 |
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Cattivo Calcio | Falcons FC | Woodbridge College | |
| 9:00pm | Top G Calcio | Casamigos Cartel | Woodbridge College |
Thursday, June 15, 2023 – Gameweek 2
Ontario Soccer Stadium (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | AFC Woodbridge | Cattivo Calcio | Ontario Soccer Stadium | |
| 9:00pm | Falcons | Top G Calcio | Ontario Soccer Stadium |
OSA #2 (7601 Martin Grove Rd – Directly in front of the Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | La Familia FC | Calcio Kings | OSA Grass #2 | |
| 9:00pm | S.S. Ladzio | Stugotz FC | OSA Grass #2 |
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Casamigos Cartel | Crodies | Woodbridge College | |
| 9:00pm | Brethrenz United | Da Shmurdas | Woodbridge College |
Thursday, June 22, 2023- Gameweek 3
Ontario Soccer Stadium (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Crodies | Top G Calcio | Ontario Soccer Stadium | |
| 9:00pm | Brethrenz United | Falcons FC | Ontario Soccer Stadium |
OSA #2 (7601 Martin Grove Rd – Directly in front of the Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | S.S. Ladzio | Casamigos Cartel | OSA Grass #2 | |
| 9:00pm | Calcio Kings | Stugotz FC | OSA Grass #2 |
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm | Da Shmurdas | Cattivo Calcio | Woodbridge College | |
| 9:00pm | La Familia FC | AFC Woodbridge | Woodbridge College |