Head to Head
| Trinidad & Tobago Premier League | 2020/03/06 22:00 | W Connection FC v AC Port Of Spain | W | 2-0 |
| Trinidad & Tobago Premier League | 2020/01/18 00:00 | AC Port Of Spain v W Connection FC | W | 0-4 |
| Trinidad & Tobago Premier League | 2018/12/08 00:00 | W Connection FC v AC Port Of Spain | W | 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 | W | 2-0 |
| Trinidad & Tobago Charity Shield | 2018/06/01 23:11 | AC Port Of Spain v W Connection FC | W | 1-7 |
| Trinidad & Tobago Premier League | 2017/10/27 22:00 | AC Port Of Spain v W Connection FC | L | 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 | 2020/03/11 22:00 | W Connection FC v Cunupia FC | W | 3-0 |
| 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 |
Away History
| Trinidad & Tobago Ascension Tournament | 2022/06/26 21:14 | Police FC TT v AC Port Of Spain | L | 3-2 |
| Trinidad & Tobago Ascension Tournament | 2022/06/18 23:15 | AC Port Of Spain v Defence Force FC | W | 4-3 |
| Trinidad & Tobago Ascension Tournament | 2022/06/11 23:13 | CSW FC v AC Port Of Spain | W | 2-3 |
| Trinidad & Tobago Ascension Tournament | 2022/06/04 21:00 | AC Port Of Spain v Real West Fort | L | 2-3 |
| Trinidad & Tobago Ascension Tournament | 2022/05/21 00:12 | La Horquetta Rangers FC v AC Port Of Spain | L | 2-1 |
| Trinidad & Tobago Ascension Tournament | 2022/05/14 21:00 | Moruga FC v AC Port Of Spain | W | 1-6 |
| Trinidad & Tobago Ascension Tournament | 2022/05/07 21:00 | AC Port Of Spain v Real West Fort | W | 2-1 |
| Trinidad & Tobago Ascension Tournament | 2022/05/01 21:00 | Police FC TT v AC Port Of Spain | L | 5-1 |