| Thursday, 14 September 2023 03:30
|
| DaCosta Cup | Lennon | 1 | - | 0 | Claude Mckay | |
| Saturday, 23 September 2023 03:30
|
| DaCosta Cup | Lennon | 0 | - | 0 | Edwin Allen | |
| Tuesday, 26 September 2023 03:30
|
| DaCosta Cup | Lennon | 3 | - | 0 | Kellitis | |
| Friday, 29 September 2023 03:30
|
| DaCosta Cup | Lennon | 0 | - | 5 | Clarendon College | |
| Wednesday, 04 October 2023 01:30
|
| DaCosta Cup | Claude Mckay | 1 | - | 3 | Lennon | |
| Saturday, 07 October 2023 03:30
|
| DaCosta Cup | Lennon | 2 | - | 1 | Thompson Town | |
| Thursday, 12 October 2023 03:00
|
| DaCosta Cup | Edwin Allen | 2 | - | 0 | Lennon | |
| Saturday, 14 October 2023 03:30
|
| DaCosta Cup | Kellitis | | - | | Lennon | |
| Tuesday, 17 October 2023 03:00
|
| DaCosta Cup | Lennon | | - | | Edwin Allen | |
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