PLAYOFFS: Tuesday, August 22, 2023
OSA #2 (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm (Group A semi-final) | Molino City (#1) | (PK) 0-0 | Dingleberries (#4) | OSA Grass #2 |
| 9:00pm (Group A semi-final) | 4B Lunch FC (#2) | 4-1 | Dubai Strikers (#3) | OSA Grass #2 |
Woodbridge College (71 Bruce St)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm (Group B semi-final) | Calcio E Pepe (#1) | 3-0 | Bobo FC (#4) | Woodbridge College |
| 9:00pm (Group B semi-final) | Bluehaven City (#2) | 2-1 | Woodford FC (#3) | Woodbridge College |
PLAYOFFS – Tuesday, August 29, 2023
OSA #2 (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm (Group A final) | Molino City ? | 1-1 (PK) | 4B Lunch FC ? | OSA Grass #2 |
| 9:15pm (Group B final) | Calcio E Pepe ? | 2-1 | Bluehaven City | OSA Grass #2 |