Home History
| World Club Friendlies | 2019/09/27 22:22 | La Horquetta SA v San Juan Jabloteh | L | 5-0 |
| World Club Friendlies | 2019/09/19 23:03 | Queen’s Park CC v San Juan Jabloteh | W | 0-3 |
| World Club Friendlies | 2019/09/07 00:02 | Santa Rosa FC v San Juan Jabloteh | D | 1-1 |
| World Club Friendlies | 2019/08/25 20:06 | Club Sando v San Juan Jabloteh | W | 3-4 |
| World Club Friendlies | 2019/08/21 20:00 | Defence Force FC v San Juan Jabloteh | L | 2-1 |
| World Club Friendlies | 2019/07/21 19:59 | San Juan Jabloteh v Police FC | W | 3-1 |
| Trinidad & Tobago Premier League | 2018/12/08 00:00 | San Juan Jabloteh v La Horquetta Rangers FC | W | 5-0 |
| Trinidad & Tobago Premier League | 2018/11/29 00:00 | San Juan Jabloteh v W Connection FC | D | 1-1 |
Away History
| 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 |
| Trinidad & Tobago Premier League 2 | 2018/11/10 23:06 | UTT FC v Cunupia FC | D | 2-2 |