Head to Head
| Trinidad & Tobago Premier League | 2020/03/11 22:00 | W Connection FC v Cunupia FC | L | 3-0 |
| Trinidad & Tobago Premier League | 2020/01/21 23:00 | Cunupia FC v W Connection FC | L | 0-2 |
| Trinidad & Tobago FA Trophy | 2017/10/22 19:36 | W Connection FC v Cunupia FC | L | 3-2 |
Home History
| Trinidad & Tobago Premier League | 2023/04/26 20:00 | Cunupia FC v Club Sando | L | 1-4 |
| Trinidad & Tobago Premier League | 2023/04/22 21:00 | Prison Service FC v Cunupia FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2023/04/16 20:00 | Defence Force FC v Cunupia FC | L | 1-0 |
| Trinidad & Tobago Premier League | 2023/04/08 20:00 | Cunupia FC v Police FC TT | L | 1-2 |
| Trinidad & Tobago Premier League | 2023/04/05 23:15 | La Horquetta Rangers FC v Cunupia FC | L | 3-0 |
| Trinidad & Tobago Premier League | 2023/04/01 20:00 | Cunupia FC v AC Port of Spain | L | 0-4 |
| Trinidad & Tobago Premier League | 2023/03/25 22:00 | Point Fortin FC v Cunupia FC | W | 1-2 |
| Trinidad & Tobago Premier League | 2023/03/22 20:00 | Cunupia FC v Central FC | L | 0-3 |
Away History
| Trinidad & Tobago Premier League | 2023/04/22 21:00 | W Connection FC v AC Port of Spain | L | 1-3 |
| Trinidad & Tobago Premier League | 2023/04/19 23:15 | Prison Service FC v W Connection FC | L | 1-0 |
| Trinidad & Tobago Premier League | 2023/04/15 20:00 | W Connection FC v Point Fortin FC | W | 1-0 |
| Trinidad & Tobago Premier League | 2023/04/08 20:00 | Club Sando v W Connection FC | L | 3-1 |
| Trinidad & Tobago Premier League | 2023/04/05 20:00 | W Connection FC v San Juan Jabloteh | W | 2-1 |
| Trinidad & Tobago Premier League | 2023/03/31 21:00 | Defence Force FC v W Connection FC | L | 2-0 |
| Trinidad & Tobago Premier League | 2023/03/25 20:00 | W Connection FC v Morvant Caledonia Utd | D | 0-0 |
| Trinidad & Tobago Premier League | 2023/03/22 23:00 | La Horquetta Rangers FC v W Connection FC | L | 2-1 |
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