Thursday, 14 September 2023 03:30
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| DaCosta Cup | Thompson Town | 0 | - | 3 | Edwin Allen | |
Wednesday, 20 September 2023 03:30
|
| DaCosta Cup | Edwin Allen | 6 | - | 0 | Kellitis | |
Saturday, 23 September 2023 03:30
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| DaCosta Cup | Lennon | 0 | - | 0 | Edwin Allen | |
Tuesday, 26 September 2023 03:30
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| DaCosta Cup | Edwin Allen | 0 | - | 2 | Clarendon College | |
Friday, 29 September 2023 03:30
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| DaCosta Cup | Edwin Allen | 7 | - | 0 | Claude Mckay | |
Wednesday, 04 October 2023 03:30
|
| DaCosta Cup | Edwin Allen | 3 | - | 1 | Thompson Town | |
Saturday, 07 October 2023 03:30
|
| DaCosta Cup | Kellitis | | - | | Edwin Allen | |
Thursday, 12 October 2023 03:00
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| DaCosta Cup | Edwin Allen | 2 | - | 0 | Lennon | |
Saturday, 14 October 2023 01:30
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| DaCosta Cup | Clarendon College | 3 | - | 0 | Edwin Allen | |
Tuesday, 17 October 2023 03:00
|
| DaCosta Cup | Lennon | | - | | Edwin Allen | |
Saturday, 21 October 2023 03:00
|
| DaCosta Cup | McGrath | 1 | - | 0 | Edwin Allen | |
Wednesday, 25 October 2023 03:00
|
| DaCosta Cup | Edwin Allen | 1 | - | 3 | McGrath | |