Head to Head
| Trinidad & Tobago Premier League | 2023/04/22 21:00 | W Connection FC v AC Port Of Spain | W | 1-3 |
| Trinidad & Tobago Premier League | 2020/03/06 22:00 | W Connection FC v AC Port Of Spain | L | 2-0 |
| Trinidad & Tobago Premier League | 2020/01/18 00:00 | AC Port Of Spain v W Connection FC | L | 0-4 |
| Trinidad & Tobago Premier League | 2018/12/08 00:00 | W Connection FC v AC Port Of Spain | L | 4-0 |
| Trinidad & Tobago Premier League | 2018/09/22 19:30 | AC Port Of Spain v W Connection FC | D | 1-1 |
| Trinidad & Tobago League Cup | 2018/06/16 20:02 | W Connection FC v AC Port Of Spain | L | 2-0 |
| Trinidad & Tobago Charity Shield | 2018/06/01 23:11 | AC Port Of Spain v W Connection FC | L | 1-7 |
| Trinidad & Tobago Premier League | 2017/10/27 22:00 | AC Port Of Spain v W Connection FC | W | 1-0 |
Home History
| 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 |
| Trinidad & Tobago Premier League | 2023/04/19 22:00 | Point Fortin FC v AC Port Of Spain | W | 0-1 |
| Trinidad & Tobago Premier League | 2023/04/15 21:00 | AC Port Of Spain v San Juan Jabloteh | W | 4-1 |
| Trinidad & Tobago Premier League | 2023/04/09 21:00 | Morvant Caledonia Utd v AC Port Of Spain | W | 1-4 |
| Trinidad & Tobago Premier League | 2023/04/05 21:00 | AC Port Of Spain v Central FC | W | 2-1 |
| Trinidad & Tobago Premier League | 2023/04/01 20:00 | Cunupia FC v AC Port Of Spain | W | 0-4 |
Away History
| 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 | W | 0-3 |
| 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 |
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