| 02/12/26 21:00 | Chapelton- : -Mount Pleasant Academy | ![]() |
| 01/12/26 02:00 | Arnett Gardens FC- : -Chapelton | ![]() |
| 22/11/26 21:00 | Chapelton- : -Cavalier FC | ![]() |
| 15/11/26 21:00 | Dunbeholden FC- : -Chapelton | ![]() |
| 09/11/26 23:30 | Chapelton- : -Racing United | ![]() |
| 01/11/26 21:00 | Tru-Juice1 : 0Chapelton |
| 25/10/26 21:00 | Portmore United0 : 0Chapelton |
| 18/10/26 22:00 | Chapelton1 : 0Treasure Beach |
| 11/10/26 22:00 | Humble Lions0 : 0Chapelton |
| 06/10/26 00:05 | Chapelton0 : 6Waterhouse FC |
| 27/09/26 22:30 | Tivoli Gardens FC1 : 1Chapelton |
| 20/09/26 22:30 | Chapelton2 : 1Molynes United |
| 06/05/26 22:30 | Chapelton2 : 7Arnett Gardens FC |
| 03/05/26 22:30 | Waterhouse FC3 : 0Chapelton |
| 26/04/26 22:30 | Chapelton6 : 2Spanish Town Police |
| 24/04/26 02:00 | Mount Pleasant Academy5 : 2Chapelton |
| 19/04/26 22:30 | Chapelton0 : 2Portmore United |
| 15/04/26 22:30 | Treasure Beach0 : 3Chapelton |
| 12/04/26 22:30 | Chapelton1 : 4Cavalier FC |
| 05/04/26 22:30 | Harbour View FC1 : 1Chapelton |
| 29/03/26 22:30 | Chapelton2 : 2Molynes United |
| 25/03/26 21:30 | Tivoli Gardens FC0 : 1Chapelton |
| 22/03/26 21:30 | Chapelton3 : 1Montego Bay United |
| 19/03/26 21:30 | Racing United3 : 0Chapelton |
| 15/03/26 21:30 | Chapelton2 : 0Dunbeholden FC |
| 08/03/26 22:00 | Cavalier FC1 : 0Chapelton |
| 01/03/26 21:30 | Chapelton0 : 1Dunbeholden FC |
| 23/02/26 23:00 | Racing United2 : 0Chapelton |
| 15/02/26 21:30 | Chapelton2 : 0Treasure Beach |
| 11/02/26 21:00 | Chapelton1 : 0Molynes United |
| 08/02/26 21:00 | Molynes United0 : 0Chapelton |
| 01/02/26 21:00 | Chapelton0 : 2Mount Pleasant Academy |
| 25/01/26 21:00 | Montego Bay United2 : 0Chapelton |
| 22/01/26 21:00 | Chapelton0 : 1Waterhouse FC |
| 18/01/26 21:00 | Spanish Town Police0 : 1Chapelton |
| 16/01/26 01:00 | Chapelton3 : 0Arnett Gardens FC |
| 11/01/26 21:00 | Portmore United0 : 0Chapelton |
| 04/01/26 21:10 | Chapelton2 : 1Harbour View FC |
| 01/01/26 21:00 | Treasure Beach0 : 1Chapelton |
| 29/12/25 18:00 | Tivoli Gardens FC2 : 0Chapelton |
| 21/12/25 21:00 | Chapelton0 : 3Cavalier FC |
| 14/12/25 21:00 | Dunbeholden FC0 : 0Chapelton |
| 10/12/25 21:00 | Chapelton0 : 0Racing United |
| 12/10/25 22:00 | Mount Pleasant Academy3 : 1Chapelton |
| 05/10/25 22:00 | Chapelton1 : 2Montego Bay United |
| 30/09/25 02:30 | Waterhouse FC3 : 0Chapelton |
| 23/09/25 00:00 | Chapelton0 : 0Spanish Town Police |
| 14/09/25 22:00 | Arnett Gardens FC1 : 0Chapelton |
| 07/09/25 22:00 | Chapelton3 : 2Portmore United |
| 31/08/25 22:00 | Harbour View FC0 : 2Chapelton |