| 1. Jornada | 15.08.2019 | Glacis United FC | - | FCB Magpies | 0:9 | ||||
| 1. Jornada | 22.08.2019 | Lincoln Red Imps | - | Glacis United FC | 8:0 | ||||
| 2. Jornada | 13.09.2019 | Glacis United FC | - | Mons Calpe S.C. | 0:5 | ||||
| 2. Jornada | 22.09.2019 | Europa Point FC | - | Glacis United FC | 0:3 |  |
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| 3. Jornada | 20.10.2019 | St. Joseph's FC | - | Glacis United FC | 8:1 | ||||
| 4. Jornada | 22.11.2019 | Glacis United FC | - | College 1975 FC | 4:0 | ||||
| 4. Jornada | 29.11.2019 | Europa FC | - | Glacis United FC | 6:2 | ||||
| 5. Jornada | 10.12.2019 | Glacis United FC | - | Lions Gibraltar | 1:3 | ||||
| 5. Jornada | 18.12.2019 | Lynx FC | - | Glacis United FC | 3:2 |  |
Gibraltar