| 1. Round | 17/09/2023 | Glacis United FC | - | Mons Calpe S.C. | 2:1 |  |
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| 4. Round | 07/10/2023 | Mons Calpe S.C. | - | Europa Point FC | 3:1 | ||||
| 5. Round | 20/10/2023 | Manchester 62 FC | - | Mons Calpe S.C. | 1:2 | ||||
| 7. Round | 04/11/2023 | Mons Calpe S.C. | - | Lincoln Red Imps | 0:2 | ||||
| 8. Round | 24/11/2023 | Lions Gibraltar | - | Mons Calpe S.C. | 0:0 |  |
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| 9. Round | 02/12/2023 | Mons Calpe S.C. | - | Europa FC | 1:0 | ||||
| 10. Round | 09/12/2023 | College 1975 FC | - | Mons Calpe S.C. | 1:3 | ||||
| 12. Round | 09/01/2024 | Mons Calpe S.C. | - | Lynx FC | 1:1 | |
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| 11. Round | 16/01/2024 | Mons Calpe S.C. | - | St. Joseph's FC | 1:1 | |
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| 13. Round | 21/01/2024 | FCB Magpies | - | Mons Calpe S.C. | 3:1 | |
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| 14. Round | 27/01/2024 | Mons Calpe S.C. | - | Glacis United FC | 5:1 |  |
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| 15. Round | 03/02/2024 | Europa Point FC | - | Mons Calpe S.C. | 1:1 | |
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| 18. Round | 23/02/2024 | Lincoln Red Imps | - | Mons Calpe S.C. | 2:1 | ||||
| 21. Round | 30/03/2024 | Mons Calpe S.C. | - | College 1975 FC | 1:0 | ||||
| 22. Round | 14/04/2024 | St. Joseph's FC | - | Mons Calpe S.C. | 1:2 |  |
Gibraltar