| Thursday, 14 September 2023 03:30
|
| DaCosta Cup | Thompson Town | 0 | - | 3 | Edwin Allen | |
| Saturday, 23 September 2023 03:30
|
| DaCosta Cup | Clarendon College | 1 | - | 0 | Thompson Town | |
| Friday, 29 September 2023 03:30
|
| DaCosta Cup | Thompson Town | 2 | - | 1 | Kellitis | |
| Wednesday, 04 October 2023 03:30
|
| DaCosta Cup | Edwin Allen | 3 | - | 1 | Thompson Town | |
| Saturday, 07 October 2023 03:30
|
| DaCosta Cup | Lennon | 2 | - | 1 | Thompson Town | |
| Tuesday, 10 October 2023 03:30
|
| DaCosta Cup | Thompson Town | 0 | - | 5 | Clarendon College | |
| Thursday, 12 October 2023 03:00
|
| DaCosta Cup | Thompson Town | 1 | - | 4 | Clarendon College | |
| Saturday, 14 October 2023 03:30
|
| DaCosta Cup | Claude Mckay | | - | | Thompson Town | |
| Tuesday, 17 October 2023 03:00
|
| DaCosta Cup | Claude Mckay | 0 | - | 2 | Thompson Town | |
SB Football 
