| 1. Round | 17/09/2023 | Lynx FC | - | Lions Gibraltar | 4:1 |  |
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| 2. Round | 23/09/2023 | Lions Gibraltar | - | St. Joseph's FC | 1:5 | |
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| 5. Round | 22/10/2023 | Glacis United FC | - | Lions Gibraltar | 3:1 | ||||
| 8. Round | 24/11/2023 | Lions Gibraltar | - | Mons Calpe S.C. | 0:0 | ||||
| 9. Round | 01/12/2023 | Lincoln Red Imps | - | Lions Gibraltar | 2:0 | |
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| 11. Round | 16/12/2023 | Lions Gibraltar | - | Europa FC | 0:5 | ||||
| 12. Round | 08/01/2024 | Lions Gibraltar | - | College 1975 FC | 1:1 | ||||
| 13. Round | 20/01/2024 | St. Joseph's FC | - | Lions Gibraltar | 3:2 | ||||
| 14. Round | 28/01/2024 | Lions Gibraltar | - | Lynx FC | 0:4 | ||||
| 15. Round | 04/02/2024 | FCB Magpies | - | Lions Gibraltar | 3:1 | |
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| 16. Round | 11/02/2024 | Lions Gibraltar | - | Glacis United FC | 1:0 | ||||
| 17. Round | 18/02/2024 | Europa Point FC | - | Lions Gibraltar | 0:0 | |
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| 19. Round | 02/03/2024 | Mons Calpe S.C. | - | Lions Gibraltar | 2:2 | ||||
| 20. Round | 08/03/2024 | Lions Gibraltar | - | Lincoln Red Imps | 0:2 | |
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| 22. Round | 13/04/2024 | Europa FC | - | Lions Gibraltar | 1:2 |  |
Northern Ireland
Gibraltar