| 1. Round | 17/09/2023 | Glacis United FC | - | Mons Calpe S.C. | 2:1 |  |
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| 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 | ||||
| 6. Round | 28/10/2023 | Europa FC | - | Glacis United FC | 3:2 | ||||
| 7. Round | 04/11/2023 | Glacis United FC | - | College 1975 FC | 1:0 | ||||
| 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 |  |
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| 10. Round | 08/12/2023 | FCB Magpies | - | Glacis United FC | 3:0 | |
England
Nigeria