Sunday, June 4, 2023 – Gameweek 1
Ontario Soccer Stadium (7601 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 8:00pm | S.S.C. Passione | Hay Equipo | OSS | Competitive | |
| 9:30pm | Strikers FC | Leafs | OSS | Women’s |
OSA Grass #2 (7601 Martin Grove Rd – Directly in front of the Ontario Soccer Centre)
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 5:00pm | Walk em’ Down FC | Tdot FC | OSA #2 | Competitive | |
| 7:00pm | Stripes FC | Tito’s Tigers | OSA #2 | Women’s |
Vaughan Grove Turf (7401 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 6:00pm | Francofoot FC | Sharks Aces | Vaughan Grove Turf | Intermediate | |
| 7:30pm | Berenstain Bears | Brown Boys FC | Vaughan Grove Turf | Intermediate | |
| 9:00pm | Unity FC | Bello Mio’s FC | Vaughan Grove Turf | Competitive |
Vaughan Grove Grass #2 (7401 Martin Grove Rd)
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 5:00pm | Etobicoke FC | Morts FC | Vaughan Grove Grass #2 | Women’s | |
| 7:00pm | Victorious Secret | S.S. Lazia | Vaughan Grove Grass #2 | Women’s |
St. Joan of Arc Turf (1 St Joan of Arc Avenue)
| Kick-off | Home Team | Score | Away Team | Venue | Division |
| 5:00pm | Cruijfftal Palace | We Dem Boys | St. Joan of Arc Turf | Recreational | |
| 6:30pm | AC Pizzelle | Joga Bonito FC | St. Joan of Arc Turf | Intermediate | |
| 8:00pm | Toronto GC | Divorced Men FC | St. Joan of Arc Turf | Recreational | |
| 9:30pm | PGFC | Alianza Lima | St. Joan of Arc Turf | Recreational |