Jamaika| 06.02.2025 | JAM D1 | Mount Pleasant | - | Chapelton Maroons FC | |
| 09.02.2025 | JAM D1 | Chapelton Maroons FC | - | Cavalier FC | |
| 12.02.2025 | JAM D1 | Tivoli Gardens | - | Chapelton Maroons FC | |
| 16.02.2025 | JAM D1 | Chapelton Maroons FC | - | Vere United | |
| 16.02.2025 | JAM D1 | Harbour View | - | Chapelton Maroons FC | |
| 19.02.2025 | JAM D1 | Chapelton Maroons FC | - | Arnett Gardens | |
| 23.02.2025 | JAM D1 | Chapelton Maroons FC | - | Montego Bay Utd | |
| 26.02.2025 | JAM D1 | Molynes United | - | Chapelton Maroons FC | |
| 02.03.2025 | JAM D1 | Chapelton Maroons FC | - | Humble Lions | |
| 05.03.2025 | JAM D1 | Portmore United | - | Chapelton Maroons FC | |
| 09.03.2025 | JAM D1 | Chapelton Maroons FC | - | Waterhouse FC | |
| 16.03.2025 | JAM D1 | Dunbeholden FC | - | Chapelton Maroons FC | |
| 23.03.2025 | JAM D1 | Racing United FC | - | Chapelton Maroons FC | |
| 30.03.2025 | JAM D1 | Chapelton Maroons FC | - | Mount Pleasant | |
| 06.04.2025 | JAM D1 | Cavalier FC | - | Chapelton Maroons FC | |
| 13.04.2025 | JAM D1 | Chapelton Maroons FC | - | Tivoli Gardens | |
| 20.04.2025 | JAM D1 | Vere United | - | Chapelton Maroons FC | |
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