Head to Head
| 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 | W | 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 | 2023/05/03 21:00 | W Connection FC v Cunupia FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2023/04/30 20:00 | Cunupia FC v W Connection FC | L | 0-3 |
| Trinidad & Tobago Premier League | 2023/04/26 20:00 | Cunupia FC v Club Sando | L | 1-4 |
| Trinidad & Tobago Premier League | 2023/04/22 21:00 | Prison Service FC v Cunupia FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2023/04/16 20:00 | Defence Force FC v Cunupia FC | L | 1-0 |
| Trinidad & Tobago Premier League | 2023/04/08 20:00 | Cunupia FC v Police FC TT | L | 1-2 |
| Trinidad & Tobago Premier League | 2023/04/05 23:15 | La Horquetta Rangers FC v Cunupia FC | L | 3-0 |
| Trinidad & Tobago Premier League | 2023/04/01 20:00 | Cunupia FC v AC Port Of Spain | L | 0-4 |
Away History
| Trinidad & Tobago Premier League | 2023/05/03 23:15 | Prison Service FC v Central FC | L | 0-3 |
| Trinidad & Tobago Premier League | 2023/04/28 21:00 | Central FC v Prison Service FC | L | 3-0 |
| Trinidad & Tobago Premier League | 2023/04/22 21:00 | Prison Service FC v Cunupia FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2023/04/19 23:15 | Prison Service FC v W Connection FC | W | 1-0 |
| Trinidad & Tobago Premier League | 2023/04/16 22:15 | Prison Service FC v Club Sando | L | 0-1 |
| Trinidad & Tobago Premier League | 2023/04/08 21:00 | Prison Service FC v Defence Force FC | L | 0-7 |
| Trinidad & Tobago Premier League | 2023/04/05 23:15 | Police FC TT v Prison Service FC | L | 5-2 |
| Trinidad & Tobago Premier League | 2023/03/31 23:15 | Prison Service FC v La Horquetta Rangers FC | L | 0-2 |