Head to Head
| Trinidad & Tobago Premier League | 2024/02/25 00:00 | Prison Service FC v Cunupia FC | L | 0-3 |
| Trinidad & Tobago Premier League | 2023/12/03 19:30 | Cunupia FC v Prison Service FC | W | 1-2 |
| Trinidad & Tobago Premier League | 2023/05/06 21:00 | Cunupia FC v Prison Service FC | W | 0-2 |
| Trinidad & Tobago Premier League | 2023/04/22 21:00 | Prison Service FC v Cunupia FC | D | 1-1 |
| World Club Friendlies | 2019/09/01 20:02 | Cunupia FC v Prison Service FC | L | 4-0 |
| Trinidad & Tobago Premier League 2 | 2018/08/19 19:59 | Cunupia FC v Prison Service FC | D | 0-0 |