| 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 | ||||
| 2. Round | 13/09/2019 | Glacis United FC | - | Mons Calpe S.C. | 0:5 | ||||
| 2. Round | 22/09/2019 | Europa Point FC | - | Glacis United FC | 0:3 |  |
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| 3. Round | 20/10/2019 | St. Joseph's FC | - | Glacis United FC | 8:1 | ||||
| 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 | 10/12/2019 | Glacis United FC | - | Lions Gibraltar | 1:3 | ||||
| 5. Round | 18/12/2019 | Lynx FC | - | Glacis United FC | 3:2 |  |
Gibraltar