| 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 |
| World Club Friendlies | 2019/08/11 20:01 | Club Sando v Prison Service FC | L | 3-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/18 20:00 | San Fernando Giants v Prison Service FC | D | 3-3 |
| Trinidad & Tobago Premier League 2 | 2018/11/10 23:32 | FC Santa Rosa v Prison Service FC | L | 5-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/04 19:25 | Petit Valley v Prison Service FC | W | 1-3 |
| Trinidad & Tobago Premier League 2 | 2018/10/28 19:05 | Prison Service FC v UTT FC | D | 2-2 |
| Trinidad & Tobago Premier League 2 | 2018/10/13 22:00 | Club Sando II v Prison Service FC | W | 0-2 |
| World Club Friendlies | 2019/09/08 19:33 | Cunupia FC v Matura Reunited | L | 4-1 |
| World Club Friendlies | 2019/07/28 20:00 | Queen’s Park CC v Matura Reunited | D | 2-2 |
| Trinidad & Tobago Premier League 2 | 2018/11/08 19:30 | Cunupia FC v Matura Reunited | D | 3-3 |
| Trinidad & Tobago Premier League 2 | 2018/10/27 00:13 | FC Santa Rosa v Matura Reunited | D | 1-1 |
| Trinidad & Tobago Premier League 2 | 2018/10/06 23:00 | UTT FC v Matura Reunited | L | 5-4 |
| Trinidad & Tobago Premier League 2 | 2018/09/16 20:03 | Queen’s Park CC v Matura Reunited | D | 5-5 |
| Trinidad & Tobago Premier League 2 | 2018/07/28 20:01 | San Fernando Giants v Matura Reunited | W | 0-2 |
| Trinidad & Tobago Premier League 2 | 2018/07/08 20:00 | Petit Valley v Matura Reunited | W | 1-2 |