Head to Head
| 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 |
| Trinidad & Tobago Premier League | 2017/07/14 23:59 | W Connection FC v AC Port Of Spain | D | 2-2 |
Home History
| Trinidad & Tobago Premier League | 2020/01/14 23:00 | AC Port Of Spain v Cunupia FC | W | 1-0 |
| Trinidad & Tobago Premier League | 2020/01/07 23:00 | AC Port Of Spain v Defence Force FC | L | 0-1 |
| Trinidad & Tobago Premier League | 2020/01/03 21:00 | AC Port Of Spain v Point Fortin FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2019/12/19 23:00 | La Horquetta Rangers FC v AC Port Of Spain | L | 7-2 |
| Trinidad & Tobago Premier League | 2019/12/13 22:00 | Central FC v AC Port Of Spain | W | 2-3 |
| Trinidad & Tobago League Cup | 2019/11/15 22:01 | San Juan Jabloteh v AC Port Of Spain | D | 2-2 |
| Trinidad & Tobago League Cup | 2019/11/10 22:53 | Cunupia FC v AC Port Of Spain | D | 0-0 |
| Trinidad & Tobago League Cup | 2019/11/01 22:00 | AC Port Of Spain v Morvant Caledonia Utd | D | 2-2 |
Away History
| Trinidad & Tobago Premier League | 2020/01/11 00:00 | Defence Force FC v W Connection FC | L | 1-0 |
| Trinidad & Tobago Premier League | 2020/01/08 00:00 | W Connection FC v La Horquetta Rangers FC | W | 3-1 |
| Trinidad & Tobago Premier League | 2020/01/04 00:00 | W Connection FC v Central FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2019/12/13 22:00 | Morvant Caledonia Utd v W Connection FC | D | 1-1 |
| Trinidad & Tobago League Cup | 2019/11/23 00:00 | Police FC TT v W Connection FC | L | 1-0 |
| Trinidad & Tobago League Cup | 2019/11/21 00:00 | W Connection FC v Central FC | L | 1-2 |
| Trinidad & Tobago League Cup | 2019/11/09 00:38 | Defence Force FC v W Connection FC | D | 2-2 |
| Trinidad & Tobago Premier League | 2018/12/08 00:00 | W Connection FC v AC Port Of Spain | W | 4-0 |