| Date | Home Team | Home Score | Away Score | Away Team | Status |
|---|---|---|---|---|---|
| April 15, 2023, 3 p.m. | Darby FC | 3 | 0 | Woodbridge Strikers | Final |
| April 20, 2023, 8:30 p.m. | Hamilton United | 1 | 2 | Darby FC | Final |
| April 28, 2023, 8 p.m. | Darby FC | 1 | 2 | Scrosoppi FC | Final |
| May 7, 2023, 8:15 p.m. | Vaughan Azzurri | 3 | 1 | Darby FC | Final |
| May 12, 2023, 8 p.m. | Darby FC | 1 | 2 | Burlington SC | Final |
| May 21, 2023, 4 p.m. | Blue Devils FC | 5 | 0 | Darby FC | Final |
| May 27, 2023, 8 p.m. | North Toronto Nitros | 2 | 1 | Darby FC | Final |
| June 3, 2023, 6 p.m. | Alliance United FC | 1 | 0 | Darby FC | Final |
| June 9, 2023, 8 p.m. | Darby FC | 2 | 1 | Master's FA | Final |
| June 16, 2023, 8:45 p.m. | St. Catharines Roma | 2 | 2 | Darby FC | Final |
| June 23, 2023, 8 p.m. | Darby FC | 0 | 1 | Guelph United | Final |
| June 27, 2023, 7:30 p.m. | Electric City FC | 1 | 0 | Darby FC | Final |
| July 2, 2023, 7 p.m. | FC London | 1 | 1 | Darby FC | Final |
| July 7, 2023, 8 p.m. | North Mississauga SC | 2 | 2 | Darby FC | Final |
| July 14, 2023, 8 p.m. | Darby FC | 2 | 2 | ProStars FC | Final |
| July 21, 2023, 8 p.m. | Darby FC | 5 | 0 | Unionville Milliken S.C. | Final |
| July 29, 2023, 4 p.m. | Darby FC | 2 | 0 | Windsor City FC | Final |
| Aug. 5, 2023, 1 p.m. | Sigma FC | 2 | 2 | Darby FC | Final |
| Aug. 11, 2023, 8 p.m. | Darby FC | 1 | 2 | Simcoe County Rovers FC | Final |
| Aug. 20, 2023, 6 p.m. | BVB IA Waterloo | 0 | 6 | Darby FC | Final |