| 1. Round | 16/01/2020 | Mons Calpe S.C. | - | College 1975 FC | 1:0 | ||||
| 3. Round | 29/01/2020 | Manchester 62 FC | - | College 1975 FC | 5:0 | ||||
| 4. Round | 06/02/2020 | College 1975 FC | - | Glacis United FC | 1:2 | ||||
| 5. Round | 20/02/2020 | Boca Gibraltar | - | College 1975 FC | 7:5 | ||||
| 7. Round | 10/03/2020 | Europa Point FC | - | College 1975 FC | 5:5 |  |
Gibraltar