| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 15.09.2026 | Matchday 1 | Matchday 1 | H | ![]() | Treasure Beach FC | W | 3:21:2 |
| 20.09.2026 | Matchday 2 | Matchday 2 | A | ![]() | Chapelton Maroons | L | 1:20:1 |
| 27.09.2026 | Matchday 3 | Matchday 3 | H | ![]() | Tru-Juice FC | L | 0:10:0 |
| 05.10.2026 | Matchday 4 | Matchday 4 | H | ![]() | Racing United | L | 0:60:2 |
| 11.10.2026 | Matchday 5 | Matchday 5 | A | ![]() | Dunbeholden FC | L | 0:10:0 |
| 20.10.2026 | Matchday 6 | Matchday 6 | H | ![]() | Cavalier | W | 1:01:0 |
| 26.10.2026 | Matchday 7 | Matchday 7 | A | ![]() | Arnett Gardens | L | 1:40:2 |
| 02.11.2026 | Matchday 8 | Matchday 8 | H | ![]() | Mount Pleasant Academy | L | 1:20:1 |
| 08.11.2026 | Matchday 9 | Matchday 9 | A | ![]() | Montego Bay | D | 2:22:2 |
| 15.11.2026 | Matchday 10 | Matchday 10 | H | ![]() | Portmore Utd. | -:- | |
| 22.11.2026 | Matchday 11 | Matchday 11 | H | ![]() | Tivoli Gardens | -:- | |
| 30.11.2026 | Matchday 12 | Matchday 12 | A | ![]() | Waterhouse | -:- | |
| 02.12.2026 | Matchday 13 | Matchday 13 | H | ![]() | Humble Lions | -:- | |
| 06.12.2026 | Matchday 14 | Matchday 14 | A | ![]() | Treasure Beach FC | -:- | |
| 10.12.2026 | Matchday 15 | Matchday 15 | H | ![]() | Chapelton Maroons | -:- | |
| 13.12.2026 | Matchday 16 | Matchday 16 | A | ![]() | Tru-Juice FC | -:- | |
Molynes United













