| Date | Home Team | Home Score | Away Score | Away Team | Status |
|---|---|---|---|---|---|
| April 23, 2023, 3 p.m. | ProStars FC | 3 | 5 | North Mississauga SC | Final |
| April 29, 2023, 6:30 p.m. | ProStars FC | 0 | 3 | Guelph Union | Final |
| May 3, 2023, 8:30 p.m. | ProStars FC | 0 | 5 | Vaughan Azzurri | Final |
| May 7, 2023, 7 p.m. | ProStars FC | 2 | 4 | Darby FC | Final |
| May 14, 2023, 4 p.m. | Blue Devils FC | 4 | 1 | ProStars FC | Final |
| May 16, 2023, 7:30 p.m. | Electric City FC | 4 | 1 | ProStars FC | Final |
| May 21, 2023, 8 p.m. | ProStars FC | 0 | 3 | Tecumseh SC | Final |
| May 28, 2023, 6 p.m. | Burlington SC | 6 | 2 | ProStars FC | Final |
| June 3, 2023, 3 p.m. | Alliance United FC | 4 | 0 | ProStars FC | Final |
| June 7, 2023, 8 p.m. | BVB IA Waterloo | 1 | 1 | ProStars FC | Final |
| June 11, 2023, 3 p.m. | Woodbridge Strikers | 6 | 1 | ProStars FC | Final |
| June 17, 2023, 7 p.m. | North Toronto Nitros | 5 | 0 | ProStars FC | Final |
| June 23, 2023, 8:45 p.m. | St. Catharines Roma | 3 | 1 | ProStars FC | Final |
| June 28, 2023, 7 p.m. | ProStars FC | 0 | 3 | Unionville Milliken SC | Final |
| July 2, 2023, 7 p.m. | ProStars FC | 1 | 4 | Hamilton United | Final |
| July 9, 2023, 7 p.m. | ProStars FC | 1 | 4 | FC London | Final |
| July 12, 2023, 8 p.m. | ProStars FC | 0 | 7 | Simcoe County | Final |
| July 16, 2023, 7 p.m. | ProStars FC | 1 | 10 | NDC-Ontario | Final |