| 2. Round | 15/09/2019 | College 1975 FC | - | FCB Magpies | 1:3 | ||||
| 2. Round | 19/09/2019 | Lincoln Red Imps | - | College 1975 FC | 9:1 | ||||
| 2. Round | 30/09/2019 | College 1975 FC | - | Manchester 62 FC | 0:3 | ||||
| 3. Round | 24/10/2019 | College 1975 FC | - | Boca Gibraltar | 0:4 | ||||
| 4. Round | 01/11/2019 | College 1975 FC | - | Europa FC | 0:12 | ||||
| 4. Round | 22/11/2019 | Glacis United FC | - | College 1975 FC | 4:0 |
Gibraltar