| 1. Round | 17/09/2023 | Glacis United FC | - | Mons Calpe S.C. | 2:1 | ||||
| 2. Round | 23/09/2023 | Manchester 62 FC | - | Glacis United FC | 5:0 | ||||
| 3. Round | 29/09/2023 | Glacis United FC | - | Europa Point FC | 3:1 | ||||
| 4. Round | 04/10/2023 | Lincoln Red Imps | - | Glacis United FC | 3:1 | ||||
| 6. Round | 28/10/2023 | Europa FC | - | Glacis United FC | 3:2 |  |
|||
| 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 | ||||
| 12. Round | 22/12/2023 | Europa Point FC | - | Glacis United FC | 2:0 | ||||
| 14. Round | 27/01/2024 | Mons Calpe S.C. | - | Glacis United FC | 5:1 | ||||
| 15. Round | 04/02/2024 | Glacis United FC | - | Lincoln Red Imps | 2:8 | ||||
| 18. Round | 25/02/2024 | College 1975 FC | - | Glacis United FC | 1:1 | |
|||
| 19. Round | 02/03/2024 | Glacis United FC | - | St. Joseph's FC | 1:3 |
Gibraltar