| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 13.09.2026 | Matchday 1 | Matchday 1 | A | ![]() | Montego Bay | L | 0:20:1 |
| 20.09.2026 | Matchday 2 | Matchday 2 | H | ![]() | Molynes United | W | 2:11:0 |
| 27.09.2026 | Matchday 3 | Matchday 3 | A | ![]() | Tivoli Gardens | D | 1:11:1 |
| 06.10.2026 | Matchday 4 | Matchday 4 | H | ![]() | Waterhouse | L | 0:60:3 |
| 11.10.2026 | Matchday 5 | Matchday 5 | A | ![]() | Humble Lions | D | 0:00:0 |
| 18.10.2026 | Matchday 6 | Matchday 6 | H | ![]() | Treasure Beach FC | W | 1:00:0 |
| 25.10.2026 | Matchday 7 | Matchday 7 | A | ![]() | Portmore Utd. | D | 0:00:0 |
| 01.11.2026 | Matchday 8 | Matchday 8 | A | ![]() | Tru-Juice FC | L | 0:10:0 |
| 09.11.2026 | Matchday 9 | Matchday 9 | H | ![]() | Racing United | D | 0:00:0 |
| 15.11.2026 | Matchday 10 | Matchday 10 | A | ![]() | Dunbeholden FC | -:- | |
| 22.11.2026 | Matchday 11 | Matchday 11 | H | ![]() | Cavalier | -:- | |
| 01.12.2026 | Matchday 12 | Matchday 12 | A | ![]() | Arnett Gardens | -:- | |
| 02.12.2026 | Matchday 13 | Matchday 13 | H | ![]() | Mount Pleasant Academy | -:- | |
| 06.12.2026 | Matchday 14 | Matchday 14 | H | ![]() | Montego Bay | -:- | |
| 10.12.2026 | Matchday 15 | Matchday 15 | A | ![]() | Molynes United | -:- | |
| 13.12.2026 | Matchday 16 | Matchday 16 | H | ![]() | Tivoli Gardens | -:- | |
Chapelton Maroons













