| 1. Round | 16/09/2023 | Europa Point FC | - | Manchester 62 FC | 1:5 | ||||
| 2. Round | 23/09/2023 | Manchester 62 FC | - | Glacis United FC | 5:0 | ||||
| 3. Round | 30/09/2023 | FCB Magpies | - | Manchester 62 FC | 2:0 | ||||
| 5. Round | 20/10/2023 | Manchester 62 FC | - | Mons Calpe S.C. | 1:2 | ||||
| 7. Round | 05/11/2023 | Manchester 62 FC | - | Lions Gibraltar | 7:0 | ||||
| 8. Round | 26/11/2023 | Europa FC | - | Manchester 62 FC | 0:1 | ||||
| 9. Round | 03/12/2023 | Manchester 62 FC | - | College 1975 FC | 4:1 |  |
|||
| 10. Round | 10/12/2023 | St. Joseph's FC | - | Manchester 62 FC | 4:0 | ||||
| 11. Round | 15/12/2023 | Manchester 62 FC | - | Lynx FC | 5:1 |  |
|||
| 14. Round | 26/01/2024 | Manchester 62 FC | - | Europa Point FC | 0:2 | ||||
| 16. Round | 09/02/2024 | Mons Calpe S.C. | - | Manchester 62 FC | 2:0 | |
|||
| 17. Round | 17/02/2024 | Manchester 62 FC | - | Lincoln Red Imps | 0:7 | |
|||
| 18. Round | 24/02/2024 | Lions Gibraltar | - | Manchester 62 FC | 2:1 | ||||
| 19. Round | 03/03/2024 | Manchester 62 FC | - | Europa FC | 1:1 | |
|||
| 21. Round | 02/04/2024 | Manchester 62 FC | - | St. Joseph's FC | 0:3 |
Gibraltar