| 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 | 22/11/2019 | Glacis United FC | - | College 1975 FC | 4:0 | ||||
| 4. Round | 28/11/2019 | College 1975 FC | - | Lions Gibraltar | 1:6 | |
|||
| 5. Round | 06/12/2019 | Lynx FC | - | College 1975 FC | 4:0 | ||||
| 5. Round | 16/12/2019 | Europa Point FC | - | College 1975 FC | 6:1 |  |
|
Gibraltar