| Tuesday, 12 September 2023 03:30
|
| DaCosta Cup | Discovery Bay High | | - | | Ocho Rios | |
| Friday, 15 September 2023 03:30
|
| DaCosta Cup | Discovery Bay High | | - | | Aabuthnott Gallimore | |
| Wednesday, 20 September 2023 03:30
|
| DaCosta Cup | Cedric Titus | | - | | Discovery Bay High | |
| Saturday, 23 September 2023 03:30
|
| DaCosta Cup | Discovery Bay High | 0 | - | 10 | York Castle | |
| Wednesday, 27 September 2023 03:30
|
| DaCosta Cup | William Knibb | 8 | - | 0 | Discovery Bay High | |
| Saturday, 30 September 2023 03:30
|
| DaCosta Cup | Browns Town | 12 | - | 1 | Discovery Bay High | |
| Wednesday, 04 October 2023 03:30
|
| DaCosta Cup | Ferncourt High | 3 | - | 1 | Discovery Bay High | |
| Friday, 06 October 2023 03:30
|
| DaCosta Cup | York Castle | | - | | Discovery Bay High | |
| Friday, 13 October 2023 03:00
|
| DaCosta Cup | Discovery Bay High | | - | | Aabuthnott Gallimore | |
SB Football 
