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 |
| Trinidad & Tobago Premier League | 2017/07/14 23:59 | W Connection FC v AC Port Of Spain | D | 2-2 |
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