Head to Head
| Trinidad & Tobago Premier League 2 | 2018/08/19 19:59 | Cunupia FC v Prison Service FC | D | 0-0 |
Home History
| World Club Friendlies | 2019/07/14 19:42 | Cunupia FC v Defence Force FC | L | 0-2 |
| Trinidad & Tobago League Cup | 2018/12/09 23:32 | FC Santa Rosa v Cunupia FC | D | 3-3 |
| Trinidad & Tobago Premier League 2 | 2018/11/18 19:31 | Cunupia FC v Petit Valley | W | 3-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/10 23:06 | UTT FC v Cunupia FC | D | 2-2 |
| Trinidad & Tobago Premier League 2 | 2018/11/08 19:30 | Cunupia FC v Matura Reunited | D | 3-3 |
| Trinidad & Tobago Premier League 2 | 2018/11/03 21:58 | Club Sando II v Cunupia FC | W | 1-2 |
| Trinidad & Tobago Premier League 2 | 2018/10/07 20:00 | Cunupia FC v Police FC II | W | 2-0 |
| Trinidad & Tobago League Cup | 2018/09/09 19:44 | Cunupia FC v Police FC II | W | 2-1 |
Away History
| World Club Friendlies | 2019/08/11 20:01 | Club Sando v Prison Service FC | L | 3-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/18 20:00 | San Fernando Giants v Prison Service FC | D | 3-3 |
| Trinidad & Tobago Premier League 2 | 2018/11/10 23:32 | FC Santa Rosa v Prison Service FC | L | 5-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/04 19:25 | Petit Valley v Prison Service FC | W | 1-3 |
| Trinidad & Tobago Premier League 2 | 2018/10/28 19:05 | Prison Service FC v UTT FC | D | 2-2 |
| Trinidad & Tobago Premier League 2 | 2018/10/13 22:00 | Club Sando II v Prison Service FC | W | 0-2 |
| Trinidad & Tobago Premier League 2 | 2018/10/07 19:31 | Prison Service FC v Queen’s Park CC | W | 4-3 |
| Trinidad & Tobago Premier League 2 | 2018/09/23 19:21 | Prison Service FC v Guaya United | D | 1-1 |
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