| 2. Round | 23/09/2023 | Lions Gibraltar | - | St. Joseph's FC | 1:5 | ||||
| 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 | ||||
| 9. Round | 03/12/2023 | Europa Point FC | - | St. Joseph's FC | 1:0 | ||||
| 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 | ||||
| 19. Round | 02/03/2024 | Glacis United FC | - | St. Joseph's FC | 1:3 |
Gibraltar