| 3. Round | 29/09/2023 | Glacis United FC | - | Europa Point FC | 3:1 |  |
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| 4. Round | 04/10/2023 | Lincoln Red Imps | - | Glacis United FC | 3:1 | |
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| 5. Round | 22/10/2023 | Glacis United FC | - | Lions Gibraltar | 3:1 | ||||
| 6. Round | 28/10/2023 | Europa FC | - | Glacis United FC | 3:2 | |
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| 8. Round | 25/11/2023 | St. Joseph's FC | - | Glacis United FC | 4:0 | ||||
| 9. Round | 02/12/2023 | Glacis United FC | - | Lynx FC | 2:0 | ||||
| 10. Round | 08/12/2023 | FCB Magpies | - | Glacis United FC | 3:0 | ||||
| 12. Round | 22/12/2023 | Europa Point FC | - | Glacis United FC | 2:0 | ||||
| 13. Round | 20/01/2024 | Glacis United FC | - | Manchester 62 FC | 0:1 | ||||
| 14. Round | 27/01/2024 | Mons Calpe S.C. | - | Glacis United FC | 5:1 | |
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| 15. Round | 04/02/2024 | Glacis United FC | - | Lincoln Red Imps | 2:8 | ||||
| 16. Round | 11/02/2024 | Lions Gibraltar | - | Glacis United FC | 1:0 | ||||
| 19. Round | 02/03/2024 | Glacis United FC | - | St. Joseph's FC | 1:3 | |
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| 20. Round | 10/03/2024 | Lynx FC | - | Glacis United FC | 2:1 | |
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| 21. Round | 30/03/2024 | Glacis United FC | - | FCB Magpies | 1:2 |
Netherlands