| 1. Round | 14/01/2020 | Boca Gibraltar | - | Europa Point FC | 2:4 |  |
|||
| 2. Round | 23/01/2020 | College 1975 FC | - | Europa Point FC | 2:6 | ||||
| 3. Round | 30/01/2020 | Europa Point FC | - | Glacis United FC | 2:1 | |
|||
| 4. Round | 08/02/2020 | Mons Calpe S.C. | - | Europa Point FC | 1:1 | ||||
| 5. Round | 19/02/2020 | Europa Point FC | - | Manchester 62 FC | 3:1 | |
|||
| 6. Round | 25/02/2020 | Europa Point FC | - | Boca Gibraltar | 2:1 | ||||
| 7. Round | 10/03/2020 | Europa Point FC | - | College 1975 FC | 5:5 |
Gibraltar