| Wednesday, 13 September 2023 03:30
|
| DaCosta Cup | Old Harbour | 0 | - | 4 | Glenmuir | |
| Saturday, 16 September 2023 03:30
|
| DaCosta Cup | Glenmuir | 5 | - | 1 | Central | |
| Tuesday, 19 September 2023 03:30
|
| DaCosta Cup | Glenmuir | 15 | - | 0 | Porus | |
| Tuesday, 26 September 2023 03:30
|
| DaCosta Cup | Denbigh | 0 | - | 2 | Glenmuir | |
| Friday, 29 September 2023 03:30
|
| DaCosta Cup | Glenmuir | 1 | - | 2 | Old Harbour | |
| Wednesday, 04 October 2023 03:30
|
| DaCosta Cup | Porus | 1 | - | 7 | Glenmuir | |
| Saturday, 07 October 2023 03:30
|
| DaCosta Cup | Central | 1 | - | 1 | Glenmuir | |
| Saturday, 14 October 2023 03:30
|
| DaCosta Cup | Glenmuir | 2 | - | 1 | Denbigh | |
| Friday, 20 October 2023 03:00
|
| DaCosta Cup | Morant Bay | 0 | - | 3 | Glenmuir | |
| Tuesday, 24 October 2023 03:00
|
| DaCosta Cup | Glenmuir | 9 | - | 0 | Morant Bay | |
| Saturday, 28 October 2023 03:00
|
| DaCosta Cup | Garvey Maceo | 1 | - | 1 | Glenmuir | |
| Wednesday, 01 November 2023 03:00
|
| DaCosta Cup | Glenmuir | 5 | - | 0 | Port Antonio | |
| Saturday, 04 November 2023 03:00
|
| DaCosta Cup | Frome Tech | 1 | - | 2 | Glenmuir | |
| Wednesday, 08 November 2023 03:00
|
| DaCosta Cup | Glenmuir | 2 | - | 0 | Manchester | |
| Saturday, 11 November 2023 03:00
|
| DaCosta Cup | Glenmuir | 1 | - | 0 | Christiana | |
| Tuesday, 14 November 2023 03:00
|
| DaCosta Cup | Clarendon College | 2 | - | 1 | Glenmuir | |
| Saturday, 25 November 2023 03:00
|
| DaCosta Cup | Dinthill Tech | 4 | - | 2 | Glenmuir | |
| Saturday, 02 December 2023 05:00
|
| DaCosta Cup | Glenmuir | 3 | - | 2 | Clarendon College | |
| Saturday, 09 December 2023 06:15
|
| DaCosta Cup | Clarendon College | 6 | - | 2 | Glenmuir | |
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