| Trinidad & Tobago Premier League 2 | 2018/09/23 19:21 | Prison Service FC v Guaya United | D | 1-1 |
| Trinidad & Tobago Premier League 2 | 2018/06/16 21:06 | Guaya United v Prison Service FC | D | 1-1 |
| 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 |
| 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 |
| World Club Friendlies | 2019/08/24 00:00 | Santa Rosa FC v Guaya United | L | 3-1 |
| Trinidad & Tobago Premier League 2 | 2018/11/15 22:00 | Police FC II v Guaya United | W | 1-2 |
| Trinidad & Tobago Premier League 2 | 2018/11/11 19:30 | Queen’s Park CC v Guaya United | D | 2-2 |
| Trinidad & Tobago Premier League 2 | 2018/10/06 20:04 | San Fernando Giants v Guaya United | W | 1-4 |
| Trinidad & Tobago Premier League 2 | 2018/09/23 19:21 | Prison Service FC v Guaya United | 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 |