| 1. Round | 17/09/2023 | Glacis United FC | - | Mons Calpe S.C. | 2:1 |  |
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| 3. Round | 29/09/2023 | Glacis United FC | - | Europa Point FC | 3:1 | ||||
| 8. Round | 25/11/2023 | St. Joseph's FC | - | Glacis United FC | 4:0 | ||||
| 10. Round | 08/12/2023 | FCB Magpies | - | Glacis United FC | 3:0 | ||||
| 17. Round | 18/02/2024 | Glacis United FC | - | Europa FC | 0:1 |  |
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| 18. Round | 25/02/2024 | College 1975 FC | - | Glacis United FC | 1:1 | |
Gibraltar