| Wednesday, 13 September 2023 03:30
|
| DaCosta Cup | Port Antonio | 0 | - | 5 | Happy Grove | |
| Saturday, 16 September 2023 03:30
|
| DaCosta Cup | Port Antonio | 3 | - | 1 | Titchfield | |
| Wednesday, 20 September 2023 03:30
|
| DaCosta Cup | Fair Prospect | 1 | - | 1 | Port Antonio | |
| Tuesday, 03 October 2023 03:30
|
| DaCosta Cup | Happy Grove | 3 | - | 2 | Port Antonio | |
| Friday, 06 October 2023 03:30
|
| DaCosta Cup | Port Antonio | 4 | - | 0 | Fair Prospect | |
| Friday, 13 October 2023 03:00
|
| DaCosta Cup | Titchfield | 0 | - | 2 | Port Antonio | |
| Saturday, 21 October 2023 03:00
|
| DaCosta Cup | Port Antonio | 1 | - | 0 | Manning's | |
| Wednesday, 25 October 2023 03:00
|
| DaCosta Cup | Manning's | 2 | - | 0 | Port Antonio | |
| Saturday, 28 October 2023 03:00
|
| DaCosta Cup | Port Antonio | 0 | - | 1 | Frome Tech | |
| Wednesday, 01 November 2023 03:00
|
| DaCosta Cup | Glenmuir | 5 | - | 0 | Port Antonio | |
| Saturday, 04 November 2023 03:00
|
| DaCosta Cup | Port Antonio | 1 | - | 4 | Garvey Maceo | |
| Wednesday, 15 November 2023 03:00
|
| DaCosta Cup | McGrath | 3 | - | 4 | Port Antonio | |
SB Football 
