| 4. Round | 05/10/2023 | Lions Gibraltar | - | FCB Magpies | 0:2 | ||||
| 5. Round | 22/10/2023 | Glacis United FC | - | Lions Gibraltar | 3:1 |  |
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| 6. Round | 28/10/2023 | Lions Gibraltar | - | Europa Point FC | 1:3 | ||||
| 7. Round | 05/11/2023 | Manchester 62 FC | - | Lions Gibraltar | 7:0 |  |
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| 13. Round | 20/01/2024 | St. Joseph's FC | - | Lions Gibraltar | 3:2 | ||||
| 14. Round | 28/01/2024 | Lions Gibraltar | - | Lynx FC | 0:4 | |
Gibraltar