Head to Head
| Trinidad & Tobago Premier League | 2020/01/29 00:00 | San Juan Jabloteh v Cunupia FC | D | 1-1 |
| Trinidad & Tobago League Cup | 2019/11/03 22:11 | San Juan Jabloteh v Cunupia FC | D | 2-2 |
Home History
| Trinidad & Tobago Premier League | 2023/03/12 20:00 | Morvant Caledonia Utd v Cunupia FC | L | 2-0 |
| Trinidad & Tobago Ascension Tournament | 2022/07/09 21:00 | Cunupia FC v Central FC | L | 1-3 |
| Trinidad & Tobago Ascension Tournament | 2022/06/25 23:18 | Defence Force FC v Cunupia FC | D | 0-0 |
| Trinidad & Tobago Ascension Tournament | 2022/06/18 21:00 | Moruga FC v Cunupia FC | D | 0-0 |
| Trinidad & Tobago Ascension Tournament | 2022/06/03 22:00 | Cunupia FC v Deportivo PF | L | 1-6 |
| Trinidad & Tobago Ascension Tournament | 2022/05/20 22:00 | Cunupia FC v CSW FC | L | 0-1 |
| Trinidad & Tobago Ascension Tournament | 2022/05/13 22:00 | La Horquetta Rangers FC v Cunupia FC | D | 1-1 |
| Trinidad & Tobago Ascension Tournament | 2022/04/30 23:00 | Defence Force FC v Cunupia FC | L | 5-0 |
Away History
| Trinidad & Tobago Premier League | 2023/03/12 22:30 | Prison Service FC v San Juan Jabloteh | D | 0-0 |
| Trinidad & Tobago Premier League | 2020/03/10 22:00 | AC Port Of Spain v San Juan Jabloteh | W | 0-1 |
| Trinidad & Tobago Premier League | 2020/03/04 22:00 | San Juan Jabloteh v Defence Force FC | L | 1-2 |
| Trinidad & Tobago Premier League | 2020/02/28 22:00 | San Juan Jabloteh v La Horquetta Rangers FC | L | 0-2 |
| Trinidad & Tobago Premier League | 2020/02/14 23:00 | Point Fortin FC v San Juan Jabloteh | L | 2-1 |
| Trinidad & Tobago Premier League | 2020/02/11 22:00 | Morvant Caledonia Utd v San Juan Jabloteh | W | 1-4 |
| Trinidad & Tobago Premier League | 2020/02/07 22:00 | Central FC v San Juan Jabloteh | L | 3-1 |
| Trinidad & Tobago Premier League | 2020/02/05 00:00 | San Juan Jabloteh v Club Sando | L | 0-5 |