| 1. Round | 16/09/2023 | St. Joseph's FC | - | Europa FC | 3:0 | ||||
| 2. Round | 23/09/2023 | Lions Gibraltar | - | St. Joseph's FC | 1:5 |  |
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| 3. Round | 28/09/2023 | St. Joseph's FC | - | Lincoln Red Imps | 1:0 | ||||
| 6. Round | 27/10/2023 | St. Joseph's FC | - | Lynx FC | 2:0 | ||||
| 7. Round | 03/11/2023 | FCB Magpies | - | St. Joseph's FC | 2:4 | ||||
| 8. Round | 25/11/2023 | St. Joseph's FC | - | Glacis United FC | 4:0 |  |
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| 9. Round | 03/12/2023 | Europa Point FC | - | St. Joseph's FC | 1:0 | ||||
| 10. Round | 10/12/2023 | St. Joseph's FC | - | Manchester 62 FC | 4:0 | ||||
| 12. Round | 21/12/2023 | Lincoln Red Imps | - | St. Joseph's FC | 1:2 | ||||
| 13. Round | 20/01/2024 | St. Joseph's FC | - | Lions Gibraltar | 3:2 | ||||
| 14. Round | 27/01/2024 | Europa FC | - | St. Joseph's FC | 0:1 | ||||
| 15. Round | 02/02/2024 | St. Joseph's FC | - | College 1975 FC | 4:1 | ||||
| 17. Round | 16/02/2024 | Lynx FC | - | St. Joseph's FC | 1:2 | ||||
| 18. Round | 24/02/2024 | St. Joseph's FC | - | FCB Magpies | 2:2 | ||||
| 19. Round | 02/03/2024 | Glacis United FC | - | St. Joseph's FC | 1:3 | ||||
| 20. Round | 09/03/2024 | St. Joseph's FC | - | Europa Point FC | 1:0 |
Gibraltar