| Trinidad & Tobago Premier League 2 | 2018/11/10 23:32 | FC Santa Rosa v Prison Service FC | W | 5-1 |
| Trinidad & Tobago League Cup | 2018/09/08 23:35 | FC Santa Rosa v Prison Service FC | W | 3-0 |
| Trinidad & Tobago League Cup | 2018/12/09 23:32 | FC Santa Rosa v Cunupia FC | D | 3-3 |
| Trinidad & Tobago Premier League 2 | 2018/11/23 23:14 | FC Santa Rosa v San Fernando Giants | W | 4-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/10 23:32 | FC Santa Rosa v Prison Service FC | W | 5-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/08 23:37 | FC Santa Rosa v Petit Valley | W | 2-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/03 23:33 | FC Santa Rosa v UTT FC | W | 3-2 |
| Trinidad & Tobago Premier League 2 | 2018/10/27 00:13 | FC Santa Rosa v Matura Reunited | D | 1-1 |
| Trinidad & Tobago Premier League 2 | 2018/10/14 19:26 | Queen’s Park CC v FC Santa Rosa | D | 1-1 |
| Trinidad & Tobago Premier League 2 | 2018/10/06 23:34 | FC Santa Rosa v RSSR FC | W | 6-0 |
| 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 |
| World Club Friendlies | 2019/08/11 20:01 | Club Sando v Prison Service FC | L | 3-1 |