N | 2023-05-27 | Harbour View |  | 0-1 |  | Dunbeholden | 3/4 | ||
U | 2023-05-20 | Portmore United |  | 1-1 | | Harbour View | HF | ||
U | 2023-05-13 | Harbour View | | 2-2 | | Portmore United | HF | ||
S | 2023-04-19 | Chapelton Maroons |  | 1-2 | | Harbour View | VF | ||
U | 2023-04-14 | Harbour View | | 1-1 | | Chapelton Maroons | VF | ||
S | 2023-03-22 | Harbour View | | 4-0 |  | Falmouth United | 1/8 |
N | 2023-03-22 | Harbour View | | 4-0 | | Falmouth United | 1/8 | ||
S | 2023-03-08 | Tru Juice FC |  | 1-2 | | Falmouth United | 1R |
