| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 15.09.2026 | Matchday 1 | Matchday 1 | H | ![]() | Arnett Gardens | W | 3:22:1 |
| 20.09.2026 | Matchday 2 | Matchday 2 | A | ![]() | Mount Pleasant Academy | W | 1:00:0 |
| 28.09.2026 | Matchday 3 | Matchday 3 | H | ![]() | Montego Bay | L | 0:10:1 |
| 05.10.2026 | Matchday 4 | Matchday 4 | A | ![]() | Molynes United | W | 6:02:0 |
| 13.10.2026 | Matchday 5 | Matchday 5 | A | ![]() | Tivoli Gardens | W | 4:33:2 |
| 20.10.2026 | Matchday 6 | Matchday 6 | H | ![]() | Waterhouse | D | 0:00:0 |
| 25.10.2026 | Matchday 7 | Matchday 7 | A | ![]() | Humble Lions | W | 2:12:1 |
| 01.11.2026 | Matchday 8 | Matchday 8 | H | ![]() | Treasure Beach FC | L | 3:42:2 |
| 09.11.2026 | Matchday 9 | Matchday 9 | A | ![]() | Chapelton Maroons | D | 0:00:0 |
| 15.11.2026 | Matchday 10 | Matchday 10 | H | ![]() | Tru-Juice FC | -:- | |
| 24.11.2026 | Matchday 11 | Matchday 11 | A | ![]() | Portmore Utd. | -:- | |
| 29.11.2026 | Matchday 12 | Matchday 12 | A | ![]() | Dunbeholden FC | -:- | |
| 03.12.2026 | Matchday 13 | Matchday 13 | H | ![]() | Cavalier | -:- | |
| 06.12.2026 | Matchday 14 | Matchday 14 | A | ![]() | Arnett Gardens | -:- | |
| 10.12.2026 | Matchday 15 | Matchday 15 | H | ![]() | Mount Pleasant Academy | -:- | |
| 13.12.2026 | Matchday 16 | Matchday 16 | A | ![]() | Montego Bay | -:- | |
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