Home History
| Trinidad e Tobago - Premier League | 2023/04/16 22:15 | Prison Service FC v Club Sando | L | 0-1 |
| Trinidad e Tobago - Premier League | 2023/04/08 21:00 | Prison Service FC v Defence Force FC | L | 0-7 |
| Trinidad e Tobago - Premier League | 2023/04/05 23:15 | Police FC TT v Prison Service FC | L | 5-2 |
| Trinidad e Tobago - Premier League | 2023/03/31 23:15 | Prison Service FC v La Horquetta Rangers FC | L | 0-2 |
| Trinidad e Tobago - Premier League | 2023/03/26 20:00 | AC Port of Spain v Prison Service FC | L | 5-0 |
| Trinidad e Tobago - Premier League | 2023/03/22 23:30 | Prison Service FC v Morvant Caledonia Utd | W | 2-1 |
| Trinidad e Tobago - Premier League | 2023/03/18 21:00 | Prison Service FC v Point Fortin FC | L | 0-2 |
| Trinidad e Tobago - Premier League | 2023/03/12 22:30 | Prison Service FC v San Juan Jabloteh | D | 0-0 |
Away History
| Trinidad e Tobago - Premier League | 2023/04/15 20:00 | W Connection FC v Point Fortin FC | W | 1-0 |
| Trinidad e Tobago - Premier League | 2023/04/08 20:00 | Club Sando v W Connection FC | L | 3-1 |
| Trinidad e Tobago - Premier League | 2023/04/05 20:00 | W Connection FC v San Juan Jabloteh | W | 2-1 |
| Trinidad e Tobago - Premier League | 2023/03/31 21:00 | Defence Force FC v W Connection FC | L | 2-0 |
| Trinidad e Tobago - Premier League | 2023/03/25 20:00 | W Connection FC v Morvant Caledonia Utd | D | 0-0 |
| Trinidad e Tobago - Premier League | 2023/03/22 23:00 | La Horquetta Rangers FC v W Connection FC | L | 2-1 |
| Trinidad e Tobago - Premier League | 2023/03/17 23:15 | Police FC TT v W Connection FC | W | 1-2 |
| Trinidad e Tobago - Premier League | 2023/03/10 21:00 | W Connection FC v Central FC | L | 0-2 |
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