| Trinidad & Tobago Premier League 2 | 2018/06/16 21:06 | Guaya United v Prison Service FC | 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 |
| Trinidad & Tobago Premier League 2 | 2018/08/11 19:32 | Prison Service FC v San Fernando Giants | W | 1-0 |
| Trinidad & Tobago Premier League 2 | 2018/07/29 19:29 | Prison Service FC v Petit Valley | W | 3-2 |
| Trinidad & Tobago Premier League 2 | 2018/07/21 22:57 | UTT FC v Prison Service FC | W | 2-3 |
| Trinidad & Tobago Premier League 2 | 2018/06/16 21:06 | Guaya United v Prison Service FC | D | 1-1 |
| Trinidad & Tobago Premier League 2 | 2018/08/24 22:29 | UTT FC v Guaya United | D | 0-0 |
| Trinidad & Tobago Premier League 2 | 2018/07/08 20:02 | Cunupia FC v Guaya United | D | 2-2 |
| Trinidad & Tobago Premier League 2 | 2018/06/30 21:05 | Guaya United v San Fernando Giants | W | 5-0 |
| Trinidad & Tobago Premier League 2 | 2018/06/23 00:09 | FC Santa Rosa v Guaya United | L | 3-0 |
| Trinidad & Tobago Premier League 2 | 2018/06/16 21:06 | Guaya United v Prison Service FC | D | 1-1 |
| Trinidad & Tobago FA Trophy | 2017/10/05 19:30 | Club Sando v Guaya United | D | 1-1 |
| Trinidad & Tobago Premier League 2 | 2017/07/02 22:02 | UTT FC v Guaya United | W | 1-2 |