| Friday, 15 September 2023 03:30
|
| DaCosta Cup | Annotto Bay | 9 | - | 0 | Carron High | |
| Saturday, 23 September 2023 03:30
|
| DaCosta Cup | St Mary Tech | 1 | - | 2 | Annotto Bay | |
| Tuesday, 26 September 2023 03:30
|
| DaCosta Cup | Tacky | 6 | - | 2 | Annotto Bay | |
| Saturday, 30 September 2023 03:30
|
| DaCosta Cup | Annotto Bay | 0 | - | 2 | Horace Clarke High | |
| Wednesday, 04 October 2023 03:30
|
| DaCosta Cup | Annotto Bay | 0 | - | 1 | Wycliffe Martin High | |
| Thursday, 05 October 2023 03:30
|
| DaCosta Cup | Annotto Bay | 2 | - | 2 | Wycliffe Martin High | |
| Saturday, 07 October 2023 03:30
|
| DaCosta Cup | Annotto Bay | | - | | Carron High | |
| Friday, 13 October 2023 03:00
|
| DaCosta Cup | Annotto Bay | 4 | - | 2 | St Mary Tech | |
| Tuesday, 17 October 2023 03:00
|
| DaCosta Cup | Annotto Bay | | - | | Carron High | |
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