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 |
Home History
| Trinidad & Tobago Premier League | 2025/01/12 21:00 | La Horquetta Rangers FC v Prison Service FC | D | 0-0 |
| Trinidad & Tobago Premier League | 2025/01/03 23:00 | San Juan Jabloteh v Prison Service FC | D | 2-2 |
| Trinidad & Tobago Premier League | 2024/12/26 23:00 | Police FC TT v Prison Service FC | L | 5-1 |
| Trinidad & Tobago Premier League | 2024/12/22 21:00 | 1976 FC Phoenix v Prison Service FC | L | 2-1 |
| Trinidad & Tobago Premier League | 2024/12/14 21:00 | Prison Service FC v Point Fortin FC | W | 2-0 |
| Trinidad & Tobago Premier League | 2024/12/08 21:00 | Prison Service FC v Club Sando | D | 1-1 |
| Trinidad & Tobago Premier League | 2024/05/10 00:10 | La Horquetta Rangers FC v Prison Service FC | L | 2-1 |
| Trinidad & Tobago Premier League | 2024/05/03 00:10 | Prison Service FC v AC Port Of Spain | D | 1-1 |
Away History
| Trinidad & Tobago Premier League | 2025/01/11 23:00 | Cunupia FC v Police FC TT | L | 0-6 |
| Trinidad & Tobago Premier League | 2025/01/03 21:00 | Point Fortin FC v Cunupia FC | L | 4-1 |
| Trinidad & Tobago Premier League | 2024/12/26 21:00 | Club Sando v Cunupia FC | L | 7-1 |
| Trinidad & Tobago Premier League | 2024/12/21 23:00 | Cunupia FC v Defence Force FC | L | 0-6 |
| Trinidad & Tobago Premier League | 2024/12/14 23:00 | Cunupia FC v Central FC | L | 0-2 |
| Trinidad & Tobago Premier League | 2024/12/08 23:00 | Cunupia FC v AC Port Of Spain | L | 1-4 |
| Trinidad & Tobago Premier League | 2024/05/19 20:00 | Defence Force FC v Cunupia FC | L | 5-1 |
| Trinidad & Tobago Premier League | 2024/05/12 21:00 | Cunupia FC v 1976 FC Phoenix | D | 2-2 |