| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 13.09.2026 | Matchday 1 | Matchday 1 | A | ![]() | Tivoli Gardens | L | 0:30:2 |
| 22.09.2026 | Matchday 2 | Matchday 2 | H | ![]() | Waterhouse | L | 0:50:2 |
| 27.09.2026 | Matchday 3 | Matchday 3 | A | ![]() | Portmore Utd. | L | 1:40:0 |
| 04.10.2026 | Matchday 4 | Matchday 4 | A | ![]() | Treasure Beach FC | D | 1:10:1 |
| 11.10.2026 | Matchday 5 | Matchday 5 | H | ![]() | Chapelton Maroons | D | 0:00:0 |
| 18.10.2026 | Matchday 6 | Matchday 6 | A | ![]() | Tru-Juice FC | L | 0:40:1 |
| 25.10.2026 | Matchday 7 | Matchday 7 | H | ![]() | Racing United | L | 1:21:2 |
| 01.11.2026 | Matchday 8 | Matchday 8 | A | ![]() | Dunbeholden FC | L | 0:30:2 |
| 08.11.2026 | Matchday 9 | Matchday 9 | H | ![]() | Cavalier | -:-abor. | |
| 15.11.2026 | Matchday 10 | Matchday 10 | H | ![]() | Arnett Gardens | -:- | |
| 22.11.2026 | Matchday 11 | Matchday 11 | A | ![]() | Mount Pleasant Academy | -:- | |
| 29.11.2026 | Matchday 12 | Matchday 12 | H | ![]() | Montego Bay | -:- | |
| 02.12.2026 | Matchday 13 | Matchday 13 | A | ![]() | Molynes United | -:- | |
| 06.12.2026 | Matchday 14 | Matchday 14 | H | ![]() | Tivoli Gardens | -:- | |
| 10.12.2026 | Matchday 15 | Matchday 15 | A | ![]() | Waterhouse | -:- | |
| 13.12.2026 | Matchday 16 | Matchday 16 | H | ![]() | Portmore Utd. | -:- | |
Humble Lions













