| 1. Round | 16/09/2023 | Europa Point FC | - | Manchester 62 FC | 1:5 |  |
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| 3. Round | 29/09/2023 | Glacis United FC | - | Europa Point FC | 3:1 | ||||
| 4. Round | 07/10/2023 | Mons Calpe S.C. | - | Europa Point FC | 3:1 | ||||
| 5. Round | 21/10/2023 | Europa Point FC | - | Lincoln Red Imps | 1:2 | ||||
| 6. Round | 28/10/2023 | Lions Gibraltar | - | Europa Point FC | 1:3 |  |
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| 8. Round | 25/11/2023 | College 1975 FC | - | Europa Point FC | 0:5 | |
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| 9. Round | 03/12/2023 | Europa Point FC | - | St. Joseph's FC | 1:0 | ||||
| 12. Round | 22/12/2023 | Europa Point FC | - | Glacis United FC | 2:0 | ||||
| 14. Round | 26/01/2024 | Manchester 62 FC | - | Europa Point FC | 0:2 | |
Gibraltar