Head to Head
| Trinidad & Tobago Premier League | 2018/10/03 00:00 | Police FC TT v W Connection FC | D | 0-0 |
| Trinidad & Tobago Premier League | 2018/08/16 00:00 | W Connection FC v Police FC TT | L | 4-0 |
| Trinidad & Tobago FA Trophy | 2017/12/09 00:03 | W Connection FC v Police FC TT | L | 3-1 |
| Trinidad & Tobago Premier League | 2017/10/24 19:32 | W Connection FC v Police FC TT | L | 2-1 |
| Trinidad & Tobago Premier League | 2017/06/30 22:00 | Police FC TT v W Connection FC | W | 1-0 |
| Trinidad & Tobago League Cup | 2017/02/09 01:50 | W Connection FC v Police FC TT | D | 1-1 |
| Trinidad & Tobago Premier League | 2016/12/16 23:59 | Police FC TT v W Connection FC | L | 1-3 |
| Trinidad & Tobago Premier League | 2016/10/11 21:57 | W Connection FC v Police FC TT | D | 2-2 |
Home History
| Trinidad & Tobago League Cup | 2019/11/16 19:28 | Police FC TT v Point Fortin FC | W | 5-0 |
| Trinidad & Tobago League Cup | 2019/11/08 22:34 | Central FC v Police FC TT | D | 2-2 |
| Trinidad & Tobago League Cup | 2019/11/02 00:05 | Police FC TT v Defence Force FC | W | 1-0 |
| Trinidad & Tobago Premier League | 2018/12/07 22:00 | Central FC v Police FC TT | L | 1-0 |
| Trinidad & Tobago Premier League | 2018/11/28 22:00 | Morvant Caledonia Utd v Police FC TT | W | 1-2 |
| Trinidad & Tobago Premier League | 2018/11/25 19:00 | AC Port Of Spain v Police FC TT | W | 1-5 |
| Trinidad & Tobago Premier League | 2018/11/09 22:00 | Police FC TT v La Horquetta Rangers FC | D | 2-2 |
| Trinidad & Tobago Premier League | 2018/11/03 00:00 | Police FC TT v Point Fortin FC | W | 4-1 |
Away History
| 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 |
| Trinidad & Tobago Premier League | 2018/11/29 00:00 | San Juan Jabloteh v W Connection FC | D | 1-1 |
| Trinidad & Tobago Premier League | 2018/11/25 22:00 | W Connection FC v Point Fortin FC | W | 8-0 |
| Trinidad & Tobago Premier League | 2018/11/09 19:30 | W Connection FC v Morvant Caledonia Utd | L | 0-1 |
| Trinidad & Tobago Premier League | 2018/11/03 00:00 | W Connection FC v Defence Force FC | D | 0-0 |
| Trinidad & Tobago Premier League | 2018/10/30 22:00 | W Connection FC v Central FC | D | 0-0 |