Head to Head
| Trinidad & Tobago Premier League | 2020/01/21 23:00 | Cunupia FC v W Connection FC | W | 0-2 |
| Trinidad & Tobago FA Trophy | 2017/10/22 19:36 | W Connection FC v Cunupia FC | W | 3-2 |
Home History
| Trinidad & Tobago Premier League | 2020/03/06 22:00 | W Connection FC v AC Port Of Spain | W | 2-0 |
| Trinidad & Tobago Premier League | 2020/03/01 20:00 | W Connection FC v Defence Force FC | L | 0-1 |
| Trinidad & Tobago Premier League | 2020/02/18 23:00 | Point Fortin FC v W Connection FC | W | 0-1 |
| Trinidad & Tobago Premier League | 2020/02/16 00:00 | La Horquetta Rangers FC v W Connection FC | L | 4-1 |
| Trinidad & Tobago Premier League | 2020/02/12 22:00 | Central FC v W Connection FC | W | 1-4 |
| Trinidad & Tobago Premier League | 2020/02/09 20:00 | W Connection FC v Point Fortin FC | W | 2-1 |
| Trinidad & Tobago Premier League | 2020/01/31 22:00 | W Connection FC v Club Sando | L | 2-3 |
| Trinidad & Tobago Premier League | 2020/01/28 22:00 | W Connection FC v Police FC TT | L | 0-4 |
Away History
| Trinidad & Tobago Premier League | 2020/03/08 20:00 | Central FC v Cunupia FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2020/03/03 23:00 | Cunupia FC v AC Port Of Spain | W | 2-1 |
| Trinidad & Tobago Premier League | 2020/02/29 00:00 | Morvant Caledonia Utd v Cunupia FC | L | 3-1 |
| Trinidad & Tobago Premier League | 2020/02/18 22:00 | Defence Force FC v Cunupia FC | L | 2-1 |
| Trinidad & Tobago Premier League | 2020/02/09 22:00 | Cunupia FC v Club Sando | W | 2-1 |
| Trinidad & Tobago Premier League | 2020/02/04 22:00 | Police FC TT v Cunupia FC | D | 0-0 |
| Trinidad & Tobago Premier League | 2020/01/31 23:00 | La Horquetta Rangers FC v Cunupia FC | L | 8-1 |
| Trinidad & Tobago Premier League | 2020/01/29 00:00 | San Juan Jabloteh v Cunupia FC | D | 1-1 |