Home History
| Trinidad & Tobago League Cup | 2019/11/03 22:11 | San Juan Jabloteh v Cunupia FC | D | 2-2 |
| World Club Friendlies | 2019/10/25 22:25 | Morvant Caledonia Utd v Cunupia FC | W | 0-1 |
| World Club Friendlies | 2019/09/14 19:39 | Cunupia FC v Morvant Caledonia Utd | W | 3-0 |
| World Club Friendlies | 2019/09/08 19:33 | Cunupia FC v Matura Reunited | W | 4-1 |
| World Club Friendlies | 2019/09/01 20:02 | Cunupia FC v Prison Service FC | W | 4-0 |
| 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 |
Away History
| Trinidad & Tobago League Cup | 2019/11/01 22:00 | AC Port Of Spain v Morvant Caledonia Utd | D | 2-2 |
| Trinidad & Tobago Premier League | 2018/12/08 00:00 | W Connection FC v AC Port Of Spain | L | 4-0 |
| Trinidad & Tobago Premier League | 2018/12/05 22:00 | Defence Force FC v AC Port Of Spain | L | 4-1 |
| Trinidad & Tobago Premier League | 2018/12/01 21:00 | AC Port Of Spain v Club Sando | L | 2-6 |
| Trinidad & Tobago Premier League | 2018/11/27 19:30 | AC Port Of Spain v Point Fortin FC | L | 1-3 |
| Trinidad & Tobago Premier League | 2018/11/25 19:00 | AC Port Of Spain v Police FC TT | L | 1-5 |
| Trinidad & Tobago Premier League | 2018/10/02 22:00 | San Juan Jabloteh v AC Port Of Spain | W | 1-2 |
| Trinidad & Tobago Premier League | 2018/09/28 22:00 | Morvant Caledonia Utd v AC Port Of Spain | L | 8-0 |