Home History
| Trinidad & Tobago Premier League 2 | 2019/12/08 19:27 | FC Santa Rosa v Prison Service FC | W | 1-2 |
| Trinidad & Tobago Premier League 2 | 2019/10/27 19:45 | Prison Service FC v Petit Valley | W | 8-0 |
| Trinidad & Tobago Premier League 2 | 2019/10/20 19:59 | Prison Service FC v Guaya United | W | 3-1 |
| Trinidad & Tobago Premier League 2 | 2019/10/17 00:01 | UTT FC v Prison Service FC | W | 0-2 |
| Trinidad & Tobago Premier League 2 | 2019/10/13 20:00 | Queen’s Park CC v Prison Service FC | D | 2-2 |
| World Club Friendlies | 2019/09/15 19:58 | Prison Service FC v Matura Reunited | W | 4-3 |
| World Club Friendlies | 2019/09/04 22:00 | La Horquetta Rangers FC v Prison Service FC | L | 4-1 |
| World Club Friendlies | 2019/09/01 20:02 | Cunupia FC v Prison Service FC | L | 4-0 |
Away 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 |
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