| Date | Home Team | Home Score | Away Score | Away Team | Status |
|---|---|---|---|---|---|
| April 22, 2023, 2:30 p.m. | Simcoe County | 5 | 1 | Guelph Union | Final |
| May 5, 2023, 9 p.m. | NDC-Ontario | 2 | 0 | Simcoe County | Final |
| May 14, 2023, 5 p.m. | Vaughan Azzurri | 1 | 0 | Simcoe County | Final |
| May 21, 2023, 2:30 p.m. | Simcoe County | 0 | 2 | Alliance United FC | Final |
| May 24, 2023, 8 p.m. | Hamilton United | 0 | 1 | Simcoe County | Final |
| May 28, 2023, 2:30 p.m. | Simcoe County | 6 | 1 | Darby FC | Final |
| June 3, 2023, 4 p.m. | Simcoe County | 3 | 2 | Tecumseh SC | Final |
| June 7, 2023, 9 p.m. | FC London | 4 | 0 | Simcoe County | Final |
| June 11, 2023, 6:30 p.m. | Simcoe County | 1 | 1 | North Mississauga SC | Final |
| June 18, 2023, 5 p.m. | Woodbridge Strikers | 1 | 1 | Simcoe County | Final |
| June 25, 2023, 6 p.m. | Burlington SC | 0 | 3 | Simcoe County | Final |
| July 2, 2023, 4 p.m. | Blue Devils FC | 0 | 0 | Simcoe County | Final |
| July 5, 2023, 9 p.m. | North Toronto Nitros | 2 | 0 | Simcoe County | Final |
| July 9, 2023, 2:30 p.m. | Simcoe County | 1 | 0 | Unionville Milliken SC | Final |
| July 12, 2023, 8 p.m. | ProStars FC | 0 | 7 | Simcoe County | Final |
| July 16, 2023, 6:30 p.m. | Simcoe County | 3 | 0 | St. Catharines Roma | Final |
| July 19, 2023, 8 p.m. | Simcoe County | 1 | 1 | Electric City FC | Final |
| July 22, 2023, 6 p.m. | BVB IA Waterloo | 3 | 0 | Simcoe County | Final |