Home History
| Trinidad & Tobago Premier League 2 | 2018/07/28 20:04 | Cunupia FC v Club Sando II | W | 2-0 |
| Trinidad & Tobago Premier League 2 | 2018/07/22 20:00 | Queen’s Park CC v Cunupia FC | L | 2-1 |
| Trinidad & Tobago Premier League 2 | 2018/07/12 23:12 | RSSR FC v Cunupia FC | W | 1-3 |
| Trinidad & Tobago Premier League 2 | 2018/07/08 20:02 | Cunupia FC v Guaya United | D | 2-2 |
| Trinidad & Tobago Premier League 2 | 2018/06/24 19:58 | Cunupia FC v Bethel Utd | W | 4-0 |
| Trinidad & Tobago Premier League 2 | 2018/06/17 20:00 | Erin FC v Cunupia FC | W | 1-2 |
| Trinidad & Tobago FA Trophy | 2017/10/22 19:36 | W Connection FC v Cunupia FC | L | 3-2 |
| Trinidad & Tobago Premier League 2 | 2017/08/27 20:23 | FC Santa Rosa v Cunupia FC | L | 2-0 |
Away History
| Trinidad & Tobago Premier League 2 | 2018/08/11 19:32 | Prison Service FC v San Fernando Giants | W | 1-0 |
| Trinidad & Tobago Premier League 2 | 2018/07/29 19:29 | Prison Service FC v Petit Valley | W | 3-2 |
| Trinidad & Tobago Premier League 2 | 2018/07/21 22:57 | UTT FC v Prison Service FC | W | 2-3 |
| Trinidad & Tobago Premier League 2 | 2018/06/16 21:06 | Guaya United v Prison Service FC | D | 1-1 |