Head to Head
| 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 | 2024/02/18 00:10 | Central FC v Prison Service FC | W | 0-4 |
| Trinidad & Tobago Premier League | 2024/01/28 23:00 | Prison Service FC v La Horquetta Rangers FC | L | 1-3 |
| Trinidad & Tobago Premier League | 2024/01/20 00:10 | AC Port Of Spain v Prison Service FC | L | 5-1 |
| Trinidad & Tobago Premier League | 2024/01/14 22:00 | Prison Service FC v Morvant Caledonia Utd | W | 2-1 |
| Trinidad & Tobago Premier League | 2024/01/06 22:00 | Point Fortin FC v Prison Service FC | L | 2-1 |
| Trinidad & Tobago Premier League | 2024/01/04 00:10 | Prison Service FC v Club Sando | L | 0-3 |
| Trinidad & Tobago Premier League | 2023/12/20 21:00 | Prison Service FC v 1976 FC Phoenix | W | 3-0 |
| Trinidad & Tobago Premier League | 2023/12/17 22:00 | Police FC TT v Prison Service FC | L | 7-0 |
Away History
| Trinidad & Tobago Premier League | 2024/02/18 21:00 | Cunupia FC v Police FC TT | L | 1-3 |
| Trinidad & Tobago Premier League | 2024/01/26 19:30 | 1976 FC Phoenix v Cunupia FC | L | 2-1 |
| Trinidad & Tobago Premier League | 2024/01/20 22:00 | Central FC v Cunupia FC | W | 1-3 |
| Trinidad & Tobago Premier League | 2024/01/07 22:00 | La Horquetta Rangers FC v Cunupia FC | L | 3-0 |
| Trinidad & Tobago Premier League | 2024/01/03 22:00 | Cunupia FC v AC Port Of Spain | L | 1-2 |
| Trinidad & Tobago Premier League | 2023/12/20 22:00 | Morvant Caledonia Utd v Cunupia FC | L | 2-0 |
| Trinidad & Tobago Premier League | 2023/12/15 22:00 | Cunupia FC v Point Fortin FC | W | 2-0 |
| Trinidad & Tobago Premier League | 2023/12/08 19:30 | Club Sando v Cunupia FC | D | 1-1 |