| 2. Round | 22/09/2023 | Europa FC | - | College 1975 FC | 0:3 |  |
|||
| 3. Round | 27/09/2023 | College 1975 FC | - | Lions Gibraltar | 2:1 | |
|||
| 4. Round | 03/10/2023 | College 1975 FC | - | St. Joseph's FC | 0:3 | |
|||
| 5. Round | 22/10/2023 | Lynx FC | - | College 1975 FC | 2:3 | |
|||
| 6. Round | 29/10/2023 | College 1975 FC | - | FCB Magpies | 2:6 | ||||
| 7. Round | 04/11/2023 | Glacis United FC | - | College 1975 FC | 1:0 | ||||
| 8. Round | 25/11/2023 | College 1975 FC | - | Europa Point FC | 0:5 | ||||
| 9. Round | 03/12/2023 | Manchester 62 FC | - | College 1975 FC | 4:1 | |
|||
| 11. Round | 17/12/2023 | Lincoln Red Imps | - | College 1975 FC | 7:0 | |
Argentina