| Trinidad & Tobago League Cup | 2018/09/08 23:35 | FC Santa Rosa v Prison Service FC | W | 3-0 |
| 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 League Cup | 2018/09/08 23:35 | FC Santa Rosa v Prison Service FC | W | 3-0 |
| Trinidad & Tobago Premier League 2 | 2018/08/09 00:03 | FC Santa Rosa v Erin FC | W | 4-1 |
| Trinidad & Tobago Premier League 2 | 2018/07/28 22:59 | UTT FC v FC Santa Rosa | W | 1-4 |
| 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 |
| Trinidad & Tobago Premier League 2 | 2018/10/07 19:31 | Prison Service FC v Queen’s Park CC | W | 4-3 |
| Trinidad & Tobago Premier League 2 | 2018/09/23 19:21 | Prison Service FC v Guaya United | D | 1-1 |
| Trinidad & Tobago League Cup | 2018/09/08 23:35 | FC Santa Rosa v Prison Service FC | L | 3-0 |
| Trinidad & Tobago Premier League 2 | 2018/08/30 19:33 | Prison Service FC v Erin FC | W | 4-0 |
| Trinidad & Tobago Premier League 2 | 2018/08/19 19:59 | Cunupia FC v Prison Service FC | D | 0-0 |