Home History
| CFU Caribbean Cup | 2023/10/25 22:00 | Moca FC v Robin Hood FC | L | 1-0 |
| CFU Caribbean Cup | 2023/10/06 00:06 | Robin Hood FC v Atletico Pantoja | W | 3-1 |
| CFU Caribbean Cup | 2023/09/28 00:06 | Harbour View FC v Robin Hood FC | L | 3-2 |
| CFU Caribbean Cup | 2023/09/22 00:06 | Dunbeholden FC v Robin Hood FC | W | 0-2 |
| CONCACAF Caribbean Cup | 2023/09/01 00:06 | Robin Hood FC v Cibao FC | W | 1-0 |
| Caribbean Club Shield | 2023/08/13 23:00 | Robin Hood FC v Golden Lion | W | 5-1 |
| Caribbean Club Shield | 2023/08/11 20:00 | Robin Hood FC v Metropolitan FA | W | 5-0 |
| Caribbean Club Shield | 2023/08/04 23:45 | Universidad O&M v Robin Hood FC | W | 1-2 |
Away History
| CFU Caribbean Cup | 2023/10/25 00:00 | Harbour View FC v Cavalier | W | 0-5 |
| America Friendlies | 2023/10/15 23:00 | Mount Pleasant FA v Cavalier | L | 3-1 |
| CFU Caribbean Cup | 2023/10/05 00:06 | Golden Lion v Cavalier | W | 2-5 |
| CFU Club Championship | 2023/09/20 00:06 | Cavalier v Moca FC | W | 3-0 |
| CFU Club Championship | 2023/08/31 22:06 | Cavalier v AC Port Of Spain | W | 2-1 |
| 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 |