| Date | Home Team | Home Score | Away Score | Away Team | Status |
|---|---|---|---|---|---|
| April 23, 2023, 8:30 p.m. | Unionville Milliken SC | 0 | 2 | Vaughan Azzurri | Final |
| April 30, 2023, 5 p.m. | Vaughan Azzurri | 2 | 0 | St. Catharines Roma | Final |
| May 3, 2023, 8:30 p.m. | ProStars FC | 0 | 5 | Vaughan Azzurri | Final |
| May 7, 2023, 4 p.m. | Vaughan Azzurri | 6 | 0 | Hamilton United | Final |
| May 14, 2023, 5 p.m. | Vaughan Azzurri | 1 | 0 | Simcoe County | Final |
| May 17, 2023, 8 p.m. | Vaughan Azzurri | 1 | 0 | Blue Devils FC | Final |
| May 24, 2023, 8 p.m. | Burlington SC | 0 | 3 | Vaughan Azzurri | Final |
| May 28, 2023, 7 p.m. | Vaughan Azzurri | 1 | 2 | Alliance United FC | Final |
| June 2, 2023, 8 p.m. | Darby FC | 0 | 0 | Vaughan Azzurri | Final |
| June 6, 2023, 9 p.m. | North Mississauga SC | 1 | 1 | Vaughan Azzurri | Final |
| June 14, 2023, 8 p.m. | Vaughan Azzurri | 2 | 1 | North Toronto Nitros | Final |
| June 17, 2023, 5:30 p.m. | FC London | 1 | 2 | Vaughan Azzurri | Final |
| June 25, 2023, 5 p.m. | Guelph Union | 1 | 5 | Vaughan Azzurri | Final |
| July 2, 2023, 1 p.m. | Vaughan Azzurri | 5 | 0 | Tecumseh SC | Final |
| July 9, 2023, 5 p.m. | Vaughan Azzurri | 5 | 2 | BVB IA Waterloo | Final |
| July 12, 2023, 9 p.m. | NDC-Ontario | 2 | 1 | Vaughan Azzurri | Final |
| July 15, 2023, 1 p.m. | Electric City FC | 1 | 2 | Vaughan Azzurri | Final |
| July 23, 2023, 5 p.m. | Vaughan Azzurri | 5 | 1 | Woodbridge Strikers | Final |