Home History
| Jamaica Premier League | 2023/01/15 20:00 | Chapelton Maroons FC v Humble Lions | L | 0-3 |
| Jamaica Premier League | 2023/01/08 20:00 | Vere United v Chapelton Maroons FC | D | 0-0 |
| Jamaica Premier League | 2023/01/01 22:30 | Chapelton Maroons FC v Arnett Gardens | L | 0-5 |
| Jamaica Premier League | 2022/12/28 20:15 | Montego Bay Utd v Chapelton Maroons FC | D | 1-1 |
| Jamaica Premier League | 2022/12/21 20:00 | Chapelton Maroons FC v Molynes United FC | W | 1-0 |
| Jamaica Premier League | 2022/12/05 22:00 | Chapelton Maroons FC v Portmore United | L | 0-1 |
| Jamaica Premier League | 2022/11/21 22:00 | Waterhouse v Chapelton Maroons FC | W | 0-1 |
| Jamaica Premier League | 2022/11/06 22:30 | Chapelton Maroons FC v Cavalier | L | 0-3 |
Away History
| Jamaica Premier League | 2023/01/15 22:30 | Dunbeholden FC v Arnett Gardens | W | 4-2 |
| Jamaica Premier League | 2023/01/08 20:15 | Montego Bay Utd v Dunbeholden FC | W | 0-2 |
| Jamaica Premier League | 2023/01/02 22:00 | Dunbeholden FC v Molynes United FC | L | 0-1 |
| Jamaica Premier League | 2022/12/28 18:00 | Dunbeholden FC v Waterhouse | D | 0-0 |
| Jamaica Premier League | 2022/12/21 22:15 | Portmore United v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2022/12/04 22:00 | Tivoli Gardens v Dunbeholden FC | W | 0-2 |
| Jamaica Premier League | 2022/11/20 22:30 | Dunbeholden FC v Cavalier | L | 1-2 |
| Jamaica Premier League | 2022/11/06 20:00 | Dunbeholden FC v Harbour View FC | L | 1-4 |