| Date | Home Team | Home Score | Away Score | Away Team | Status |
|---|---|---|---|---|---|
| April 15, 2023, 3 p.m. | Darby FC | 3 | 0 | Woodbridge Strikers | Final |
| April 21, 2023, 8 p.m. | North Mississauga SC | 1 | 1 | Woodbridge Strikers | Final |
| April 30, 2023, 6:30 p.m. | Simcoe County Rovers FC | 1 | 3 | Woodbridge Strikers | Final |
| May 3, 2023, 9 p.m. | Woodbridge Strikers | 3 | 0 | Unionville Milliken S.C. | Final |
| May 6, 2023, 8 p.m. | Master's FA | 0 | 0 | Woodbridge Strikers | Final |
| May 13, 2023, 9 p.m. | Scrosoppi FC | 4 | 0 | Woodbridge Strikers | Final |
| May 21, 2023, 7 p.m. | Woodbridge Strikers | 3 | 2 | BVB IA Waterloo | Final |
| May 28, 2023, 2 p.m. | Woodbridge Strikers | 0 | 2 | Vaughan Azzurri | Final |
| June 3, 2023, 8 p.m. | North Toronto Nitros | 1 | 1 | Woodbridge Strikers | Final |
| June 10, 2023, 7 p.m. | ProStars FC | 1 | 1 | Woodbridge Strikers | Final |
| June 18, 2023, 6 p.m. | Burlington SC | 1 | 1 | Woodbridge Strikers | Final |
| June 25, 2023, 7 p.m. | Woodbridge Strikers | 2 | 1 | Sigma FC | Final |
| July 2, 2023, 7 p.m. | Woodbridge Strikers | 1 | 4 | Electric City FC | Final |
| July 5, 2023, 7 p.m. | Blue Devils FC | 0 | 2 | Woodbridge Strikers | Final |
| July 9, 2023, 7 p.m. | Woodbridge Strikers | 2 | 3 | St. Catharines Roma | Final |
| July 16, 2023, 7 p.m. | Woodbridge Strikers | 2 | 0 | Alliance United FC | Final |
| July 22, 2023, 8 p.m. | FC London | 3 | 2 | Woodbridge Strikers | Final |
| Aug. 6, 2023, 5 p.m. | Woodbridge Strikers | 1 | 1 | Windsor City FC | Final |
| Aug. 13, 2023, 5:30 p.m. | Guelph United | 2 | 2 | Woodbridge Strikers | Final |
| Aug. 20, 2023, 7 p.m. | Woodbridge Strikers | 1 | 1 | Hamilton United | Final |