| 2. Round | 22/09/2023 | Europa FC | - | College 1975 FC | 0:3 | ||||
| 3. Round | 27/09/2023 | College 1975 FC | - | Lions Gibraltar | 2:1 | ||||
| 4. Round | 03/10/2023 | College 1975 FC | - | St. Joseph's FC | 0:3 | ||||
| 5. Round | 22/10/2023 | Lynx FC | - | College 1975 FC | 2:3 | ||||
| 6. Round | 29/10/2023 | College 1975 FC | - | FCB Magpies | 2:6 |  |
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| 7. Round | 04/11/2023 | Glacis United FC | - | College 1975 FC | 1:0 | ||||
| 8. Round | 25/11/2023 | College 1975 FC | - | Europa Point FC | 0:5 | ||||
| 9. Round | 03/12/2023 | Manchester 62 FC | - | College 1975 FC | 4:1 |  |
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| 10. Round | 09/12/2023 | College 1975 FC | - | Mons Calpe S.C. | 1:3 | ||||
| 11. Round | 17/12/2023 | Lincoln Red Imps | - | College 1975 FC | 7:0 | |
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| 12. Round | 08/01/2024 | Lions Gibraltar | - | College 1975 FC | 1:1 | |
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| 13. Round | 19/01/2024 | College 1975 FC | - | Europa FC | 2:3 | |
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| 15. Round | 02/02/2024 | St. Joseph's FC | - | College 1975 FC | 4:1 | ||||
| 16. Round | 10/02/2024 | College 1975 FC | - | Lynx FC | 0:2 | ||||
| 17. Round | 17/02/2024 | FCB Magpies | - | College 1975 FC | 7:2 | ||||
| 18. Round | 25/02/2024 | College 1975 FC | - | Glacis United FC | 1:1 |  |
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| 20. Round | 10/03/2024 | College 1975 FC | - | Manchester 62 FC | 2:4 |
Spain