| 2. Round | 24/09/2023 | Lincoln Red Imps | - | Lynx FC | 3:2 | ||||
| 3. Round | 28/09/2023 | St. Joseph's FC | - | Lincoln Red Imps | 1:0 | ||||
| 4. Round | 04/10/2023 | Lincoln Red Imps | - | Glacis United FC | 3:1 |  |
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| 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 |  |
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| 6. Round | 29/10/2023 | Lincoln Red Imps | - | Manchester 62 FC | 5:0 | ||||
| 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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| 12. Round | 21/12/2023 | Lincoln Red Imps | - | St. Joseph's FC | 1:2 | ||||
| 13. Round | 21/01/2024 | Lynx FC | - | Lincoln Red Imps | 0:3 | ||||
| 15. Round | 04/02/2024 | Glacis United FC | - | Lincoln Red Imps | 2:8 | ||||
| 16. Round | 10/02/2024 | Lincoln Red Imps | - | Europa Point FC | 1:0 | ||||
| 17. Round | 17/02/2024 | Manchester 62 FC | - | Lincoln Red Imps | 0:7 | ||||
| 18. Round | 23/02/2024 | Lincoln Red Imps | - | Mons Calpe S.C. | 2:1 | |
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| 20. Round | 08/03/2024 | Lions Gibraltar | - | Lincoln Red Imps | 0:2 | ||||
| 21. Round | 31/03/2024 | Lincoln Red Imps | - | Europa FC | 2:1 | ||||
| 22. Round | 13/04/2024 | College 1975 FC | - | Lincoln Red Imps | 0:6 |
Gibraltar