| Wednesday, 13 September 2023 03:30
|
| DaCosta Cup | Port Antonio | 0 | - | 5 | Happy Grove | |
| Thursday, 21 September 2023 03:30
|
| DaCosta Cup | Happy Grove | 7 | - | 0 | Titchfield | |
| Tuesday, 03 October 2023 03:30
|
| DaCosta Cup | Happy Grove | 3 | - | 2 | Port Antonio | |
| Saturday, 07 October 2023 03:30
|
| DaCosta Cup | Titchfield | 0 | - | 1 | Happy Grove | |
| Friday, 13 October 2023 03:00
|
| DaCosta Cup | Fair Prospect | 2 | - | 3 | Happy Grove | |
| Saturday, 14 October 2023 03:30
|
| DaCosta Cup | Fair Prospect | | - | | Happy Grove | |
| Saturday, 21 October 2023 03:00
|
| DaCosta Cup | Ocho Rios | 1 | - | 2 | Happy Grove | |
| Wednesday, 25 October 2023 03:00
|
| DaCosta Cup | Happy Grove | 2 | - | 2 | Ocho Rios | |
| Saturday, 28 October 2023 03:00
|
| DaCosta Cup | Happy Grove | 2 | - | 3 | B.B. Coke | |
| Wednesday, 01 November 2023 03:00
|
| DaCosta Cup | Happy Grove | | - | | Tacky | |
| Thursday, 02 November 2023 03:00
|
| DaCosta Cup | Happy Grove | 4 | - | 2 | Tacky | |
| Saturday, 04 November 2023 03:00
|
| DaCosta Cup | Manchester | 2 | - | 0 | Happy Grove | |
| Wednesday, 15 November 2023 03:00
|
| DaCosta Cup | Happy Grove | 2 | - | 0 | Mile Gully | |
| Thursday, 23 November 2023 03:00
|
| DaCosta Cup | Happy Grove | 1 | - | 0 | Christiana | |
| Wednesday, 29 November 2023 03:00
|
| DaCosta Cup | Happy Grove | 0 | - | 4 | Frome Tech | |
SB Football 
