| 2. Round | 24/09/2023 | Lincoln Red Imps | - | Lynx FC | 3:2 | ||||
| 4. Round | 04/10/2023 | Lincoln Red Imps | - | Glacis United FC | 3:1 | ||||
| 5. Round | 21/10/2023 | Europa Point FC | - | Lincoln Red Imps | 1:2 | ||||
| 1. Round | 25/10/2023 | FCB Magpies | - | Lincoln Red Imps | 0:0 | ||||
| 6. Round | 29/10/2023 | Lincoln Red Imps | - | Manchester 62 FC | 5:0 |  |
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| 7. Round | 04/11/2023 | Mons Calpe S.C. | - | Lincoln Red Imps | 0:2 | ||||
| 9. Round | 01/12/2023 | Lincoln Red Imps | - | Lions Gibraltar | 2:0 | ||||
| 10. Round | 09/12/2023 | Europa FC | - | Lincoln Red Imps | 1:4 | ||||
| 11. Round | 17/12/2023 | Lincoln Red Imps | - | College 1975 FC | 7:0 | |
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| 13. Round | 21/01/2024 | Lynx FC | - | Lincoln Red Imps | 0:3 | ||||
| 22. Round | 13/04/2024 | College 1975 FC | - | Lincoln Red Imps | 0:6 |
Gibraltar