Sunday, August 27, 2023 – PLAYOFFS
- 1st and 2nd place receive byes:
- Competitive: S.S.C. Passione, Tdot FC
- Intermediate: Sharks Aces, The Berenstain Bears FC
- Recreational: Toronto GC, PGFC
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 5:00pm | Cruijfftal Palace | 0-0 (PK) | Bandidos Retirados | Vaughan Grove Turf | Recreational |
| 6:30pm | Brown Boys FC | 3-0 | Francofoot FC | Vaughan Grove Turf | Intermediate |
| 8:00pm | Joga Bonito FC | 3-0 | AC Pizzelle | Vaughan Grove Turf | Intermediate |
| 9:30pm | We Dem Boys | 4-2 | Divorced Men FC | Vaughan Grove Turf | Recreational |
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 8:00pm | Hay Equipo | 1-0 | Walk ‘Em Down FC | Ontario Soccer Stadium | Competitive |
| 9:30pm | Unity FC | 1-2 | Bello Mio’s FC | Ontario Soccer Stadium | Competitive |
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 5:00pm | Stripes FC | 2-1 | Victorious Secret | St. Joan of Arc Turf | Women’s |
| 6:30pm | Tito’s Tiger | 0-1 | Etobicoke FC | St. Joan of Arc Turf | Women’s |
| 8:00pm | S.S. Lazia | 3-0 | Morts FC | St. Joan of Arc Turf | Women’s |
| 9:30pm | LTS | 4-0 | Strikers FC | St. Joan of Arc Turf | Women’s |
Sunday, September 10, 2023 – PLAYOFFS
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 6:00pm | S.S.C. Passione | 7-0 | Bello Mio’s FC | Vaughan Grove Turf | Competitive |
| 7:30pm | The Berenstain Bears FC | 0-3 | Brown Boys FC | Vaughan Grove Turf | Intermediate |
| 9:00pm | Sharks Aces | 1-0 | Joga Bonito FC | Vaughan Grove Turf | Intermediate |
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 9:30pm | Tdot FC | 4-3 | Hay Equipo | Ontario Soccer Stadium | Competitive |
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 6:00pm | PGFC | 3-3 (PK) | We Dem Boys | OSA #2 | Recreational |
| 8:00pm | Toronto GC ? | 1-3 | Bandidos Retirados | OSA #2 | Recreational |
| Kick-off | Home Team | Score | Away Team | Venue | Division |
7:00pm
(Women B Final) | S.S. Lazia ? | 2-3 | LTS ? | Vaughan Grove Grass | Women’s |
8:30pm
(Women A Final) | Stripes FC ? | 0-1 | Etobicoke FC ? | Vaughan Grove Grass | Women’s |
Sunday, September 17, 2023 – FINALS
Vaughan Grove Turf (7401 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 5:00pm | We Dem Boys | 1-0 | Bandidos Retirados | Vaughan Grove Turf | Recreational |
| 7:00pm | Sharks Aces ?? | 2-0 | Brown Boys FC | Vaughan Grove Turf | Intermediate |
| 9:00pm | S.S.C. Passione ?? | 2-0 | Tdot FC | Vaughan Grove Turf | Competitive |
