PLAYOFFS: Thursday, September 7, 2023
Ontario Soccer Stadium (7601 Martin Grove Rd) – Champions League semi-finals
| Kick-off | Home Team | Score | Away Team | Venue |
| 8:00pm (semi-final A) | Brethrenz United (1st) | 2-1 | Calcio Kings (4th) | Ontario Soccer Stadium |
| 9:30pm (semi-final B) | La Familia FC (2nd) | 2-0 | Da Shmurdas (3rd) | Ontario Soccer Stadium |
OSA #2 (7601 Martin Grove Rd – Directly in front of the Soccer Centre) – Europa League semi-finals
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm (semi-final C) | AFC Woodbridge (5th) | 2-2 (PK) | Casamigos Cartel (8th) | OSA Grass #2 |
| 9:00pm (semi-final D) | Crodies (6th) | 1-0 | Top G Calcio (7th) | OSA Grass #2 |
Woodbridge College (71 Bruce St) – Conference League semi-finals
| Kick-off | Home Team | Score | Away Team | Venue |
| 7:30pm (semi-final E) | Falcons FC (9th) | 4-0 | Stugotz (12th) | Woodbridge College |
| 9:00pm (semi-final F) | Cattivo Calcio (10th) | 3-0 | S.S. Ladzio (11th) | Woodbridge College |
PLAYOFFS: Thursday, September 14, 2023
Ontario Soccer Stadium (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue |
| 8:00pm (Champions League Final) | Brethrenz United ?? | 2-1 | La Familia FC | Ontario Soccer Stadium |
| 9:30pm (Europa League Final) | Casamigos Cartel | 1-3 | Crodies ? | Ontario Soccer Stadium |
OSA #2 (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue |
| 8:30pm (Conference League Final) | Falcons FC ? | 1-0 | Cattivo Calcio | OSA Grass #2 |