| 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 | ||||
| 5. Round | 22/10/2023 | Glacis United FC | - | Lions Gibraltar | 3:1 |  |
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| 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 | |
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| 16. Round | 11/02/2024 | Lions Gibraltar | - | Glacis United FC | 1:0 |  |
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| 17. Round | 18/02/2024 | Glacis United FC | - | Europa FC | 0:1 | ||||
| 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 | ||||
| 20. Round | 10/03/2024 | Lynx FC | - | Glacis United FC | 2:1 |
Bermuda