| Tuesday, 12 September 2023 03:30
|
| DaCosta Cup | Aabuthnott Gallimore | 0 | - | 5 | York Castle | |
| Friday, 15 September 2023 03:30
|
| DaCosta Cup | Browns Town | | - | | York Castle | |
| Wednesday, 20 September 2023 03:30
|
| DaCosta Cup | York Castle | 3 | - | 0 | Ferncourt High | |
| Saturday, 23 September 2023 03:30
|
| DaCosta Cup | Discovery Bay High | 0 | - | 10 | York Castle | |
| Tuesday, 26 September 2023 03:30
|
| DaCosta Cup | Ocho Rios | | - | | York Castle | |
| Saturday, 30 September 2023 03:30
|
| DaCosta Cup | York Castle | 2 | - | 2 | Cedric Titus | |
| Tuesday, 03 October 2023 03:30
|
| DaCosta Cup | York Castle | | - | | William Knibb | |
| Wednesday, 04 October 2023 03:30
|
| DaCosta Cup | York Castle | 0 | - | 2 | William Knibb | |
| Friday, 06 October 2023 03:30
|
| DaCosta Cup | York Castle | | - | | Discovery Bay High | |
| Tuesday, 10 October 2023 03:30
|
| DaCosta Cup | Aabuthnott Gallimore | | - | | York Castle | |
| Friday, 13 October 2023 03:00
|
| DaCosta Cup | York Castle | 3 | - | 1 | Ferncourt High | |
SB Football 
