| 2. Round | 22/09/2019 | Europa Point FC | - | Glacis United FC | 0:3 | ||||
| 4. Round | 22/11/2019 | Glacis United FC | - | College 1975 FC | 4:0 | ||||
| 4. Round | 29/11/2019 | Europa FC | - | Glacis United FC | 6:2 | ||||
| 5. Round | 05/12/2019 | Glacis United FC | - | Boca Gibraltar | 0:2 | ||||
| 5. Round | 10/12/2019 | Glacis United FC | - | Lions Gibraltar | 1:3 | ||||
| 5. Round | 18/12/2019 | Lynx FC | - | Glacis United FC | 3:2 |
Gibraltar