Head to Head
| Trinidad & Tobago Premier League | 2023/04/01 20:00 | Cunupia FC v AC Port Of Spain | W | 0-4 |
| Trinidad & Tobago Ascension Tournament | 2022/04/22 22:00 | AC Port Of Spain v Cunupia FC | L | 1-4 |
| Trinidad & Tobago Premier League | 2020/03/03 23:00 | Cunupia FC v AC Port Of Spain | L | 2-1 |
| Trinidad & Tobago Premier League | 2020/01/14 23:00 | AC Port Of Spain v Cunupia FC | W | 1-0 |
| Trinidad & Tobago League Cup | 2019/11/10 22:53 | Cunupia FC v AC Port Of Spain | D | 0-0 |
Home History
| Trinidad & Tobago Premier League | 2023/05/25 23:15 | Central FC v AC Port Of Spain | W | 2-3 |
| Trinidad & Tobago Premier League | 2023/05/19 21:00 | AC Port Of Spain v Morvant Caledonia Utd | W | 5-1 |
| Trinidad & Tobago Premier League | 2023/05/13 21:00 | San Juan Jabloteh v AC Port Of Spain | W | 1-3 |
| Trinidad & Tobago Premier League | 2023/05/10 21:00 | AC Port Of Spain v Point Fortin FC | W | 2-0 |
| Trinidad & Tobago Premier League | 2023/05/06 21:00 | AC Port Of Spain v W Connection FC | W | 3-0 |
| Trinidad & Tobago Premier League | 2023/05/03 23:15 | La Horquetta Rangers FC v AC Port Of Spain | L | 3-2 |
| Trinidad & Tobago Premier League | 2023/04/30 20:00 | AC Port Of Spain v La Horquetta Rangers FC | W | 2-1 |
| Trinidad & Tobago Premier League | 2023/04/22 21:00 | W Connection FC v AC Port Of Spain | W | 1-3 |
Away History
| Trinidad & Tobago Premier League | 2023/05/25 21:00 | Cunupia FC v La Horquetta Rangers FC | L | 1-4 |
| Trinidad & Tobago Premier League | 2023/05/19 23:15 | Police FC TT v Cunupia FC | L | 2-1 |
| Trinidad & Tobago Premier League | 2023/05/13 23:15 | Cunupia FC v Defence Force FC | L | 0-2 |
| Trinidad & Tobago Premier League | 2023/05/10 20:00 | Club Sando v Cunupia FC | L | 1-0 |
| Trinidad & Tobago Premier League | 2023/05/06 21:00 | Cunupia FC v Prison Service FC | L | 0-2 |
| Trinidad & Tobago Premier League | 2023/05/03 21:00 | W Connection FC v Cunupia FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2023/04/30 20:00 | Cunupia FC v W Connection FC | L | 0-3 |
| Trinidad & Tobago Premier League | 2023/04/26 20:00 | Cunupia FC v Club Sando | L | 1-4 |
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