| 1. Round | 15/08/2019 | Glacis United FC | - | FCB Magpies | 0:9 | ||||
| 1. Round | 22/08/2019 | Lincoln Red Imps | - | Glacis United FC | 8:0 | ||||
| 3. Round | 20/10/2019 | St. Joseph's FC | - | Glacis United FC | 8:1 | ||||
| 3. Round | 26/10/2019 | Glacis United FC | - | Manchester 62 FC | 2:3 | ||||
| 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