| 2. Round | 23/09/2023 | Lions Gibraltar | - | St. Joseph's FC | 1:5 | ||||
| 3. Round | 27/09/2023 | College 1975 FC | - | Lions Gibraltar | 2:1 | ||||
| 4. Round | 05/10/2023 | Lions Gibraltar | - | FCB Magpies | 0:2 | ||||
| 5. Round | 22/10/2023 | Glacis United FC | - | Lions Gibraltar | 3:1 |  |
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| 6. Round | 28/10/2023 | Lions Gibraltar | - | Europa Point FC | 1:3 | ||||
| 7. Round | 05/11/2023 | Manchester 62 FC | - | Lions Gibraltar | 7:0 | ||||
| 9. Round | 01/12/2023 | Lincoln Red Imps | - | Lions Gibraltar | 2:0 |
England
Australia