| 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 28, 2023, 8 p.m. | Darby FC | 1 | 3 | Unionville Milliken SC | Final |
| May 6, 2023, 6 p.m. | Alliance United FC | 2 | 1 | Unionville Milliken SC | Final |
| May 14, 2023, 6 p.m. | Unionville Milliken SC | 0 | 5 | BVB IA Waterloo | Final |
| May 23, 2023, 7 p.m. | Guelph Union | 2 | 1 | Unionville Milliken SC | Final |
| May 28, 2023, 8:30 p.m. | Unionville Milliken SC | 0 | 4 | North Toronto Nitros | Final |
| June 3, 2023, 2 p.m. | Electric City FC | 3 | 1 | Unionville Milliken SC | Final |
| June 10, 2023, 9 p.m. | Unionville Milliken SC | 0 | 2 | NDC-Ontario | Final |
| June 14, 2023, 8:30 p.m. | Tecumseh SC | 4 | 1 | Unionville Milliken SC | Final |
| June 18, 2023, 8:30 p.m. | Unionville Milliken SC | 2 | 1 | Burlington SC | Final |
| June 25, 2023, 8:30 p.m. | Unionville Milliken SC | 3 | 0 | Hamilton United | Final |
| June 28, 2023, 7 p.m. | ProStars FC | 0 | 3 | Unionville Milliken SC | Final |
| July 2, 2023, 3 p.m. | FC London | 4 | 2 | Unionville Milliken SC | Final |
| July 9, 2023, 2:30 p.m. | Simcoe County | 1 | 0 | Unionville Milliken SC | Final |
| July 12, 2023, 9 p.m. | Woodbridge Strikers | 0 | 3 | Unionville Milliken SC | Final |
| July 15, 2023, 7 p.m. | North Mississauga SC | 4 | 3 | Unionville Milliken SC | Final |
| July 19, 2023, 9 p.m. | Unionville Milliken SC | 2 | 0 | Blue Devils FC | Final |
| July 22, 2023, 8:30 p.m. | Unionville Milliken SC | 2 | 0 | St. Catharines Roma | Final |