| Date | Home Team | Home Score | Away Score | Away Team | Status |
|---|---|---|---|---|---|
| April 15, 2023, noon | Hamilton United | 3 | 5 | Sigma FC | Final |
| April 20, 2023, 8:30 p.m. | Hamilton United | 1 | 2 | Darby FC | Final |
| April 26, 2023, 8 p.m. | Hamilton United | 0 | 0 | Vaughan Azzurri | Final |
| May 5, 2023, 8 p.m. | North Mississauga SC | 2 | 3 | Hamilton United | Final |
| May 17, 2023, 8 p.m. | Hamilton United | 1 | 3 | North Toronto Nitros | Final |
| May 20, 2023, 7 p.m. | Hamilton United | 1 | 1 | FC London | Final |
| May 24, 2023, 9 p.m. | Unionville Milliken S.C. | 0 | 1 | Hamilton United | Final |
| May 28, 2023, 6:30 p.m. | Simcoe County Rovers FC | 2 | 1 | Hamilton United | Final |
| June 10, 2023, 2 p.m. | Electric City FC | 0 | 0 | Hamilton United | Final |
| June 14, 2023, 8:45 p.m. | St. Catharines Roma | 3 | 2 | Hamilton United | Final |
| June 18, 2023, 4 p.m. | Hamilton United | 1 | 2 | Windsor City FC | Final |
| June 25, 2023, 7 p.m. | Hamilton United | 1 | 0 | Master's FA | Final |
| July 2, 2023, 7 p.m. | Hamilton United | 8 | 1 | BVB IA Waterloo | Final |
| July 16, 2023, 4 p.m. | Blue Devils FC | 1 | 3 | Hamilton United | Final |
| July 22, 2023, 7 p.m. | Hamilton United | 2 | 0 | ProStars FC | Final |
| Aug. 1, 2023, 8 p.m. | Guelph United | 2 | 2 | Hamilton United | Final |
| Aug. 6, 2023, 6 p.m. | Burlington SC | 3 | 1 | Hamilton United | Final |
| Aug. 11, 2023, 8 p.m. | Hamilton United | 2 | 0 | Alliance United FC | Final |
| Aug. 16, 2023, 9 p.m. | Scrosoppi FC | 5 | 0 | Hamilton United | Final |
| Aug. 20, 2023, 7 p.m. | Woodbridge Strikers | 1 | 1 | Hamilton United | Final |