Home History
| CFU Caribbean Cup | 2023/08/25 00:06 | Defence Force FC v Cavalier | D | 1-1 |
| Jamaica Premier League | 2023/06/12 00:00 | Mount Pleasant FA v Cavalier | L | 2-1 |
| Jamaica Premier League | 2023/06/05 01:00 | Cavalier v Harbour View FC | W | 2-0 |
| Jamaica Premier League | 2023/05/29 22:00 | Harbour View FC v Cavalier | W | 0-1 |
| Jamaica Cup | 2023/05/27 01:00 | Cavalier v Portmore United | L | 0-2 |
| Jamaica Cup | 2023/05/19 22:00 | Dunbeholden FC v Cavalier | W | 0-3 |
| Jamaica Cup | 2023/05/13 01:00 | Cavalier v Dunbeholden FC | W | 1-0 |
| Jamaica Premier League | 2023/05/07 20:15 | Montego Bay Utd v Cavalier | W | 1-2 |
Away History
| CFU Caribbean Cup | 2023/08/25 14:00 | Moca FC v AC Port Of Spain | L | 1-0 |
| Trinidad & Tobago Premier League | 2023/06/14 21:00 | AC Port Of Spain v Club Sando | W | 3-2 |
| Trinidad & Tobago Premier League | 2023/06/10 23:15 | Police FC TT v AC Port Of Spain | D | 1-1 |
| Trinidad & Tobago Premier League | 2023/05/28 20:00 | AC Port Of Spain v Cunupia FC | W | 4-0 |
| Trinidad & Tobago Premier League | 2023/05/25 23:15 | Central FC v AC Port Of Spain | W | 2-3 |
| Trinidad & Tobago Premier League | 2023/05/19 21:00 | AC Port Of Spain v Morvant Caledonia Utd | W | 5-1 |
| Trinidad & Tobago Premier League | 2023/05/13 21:00 | San Juan Jabloteh v AC Port Of Spain | W | 1-3 |
| Trinidad & Tobago Premier League | 2023/05/10 21:00 | AC Port Of Spain v Point Fortin FC | W | 2-0 |