| 1. Round | 15/08/2019 | Glacis United FC | - | FCB Magpies | 0:9 | ||||
| 1. Round | 23/08/2019 | FCB Magpies | - | Lions Gibraltar | 2:0 | ||||
| 2. Round | 15/09/2019 | College 1975 FC | - | FCB Magpies | 1:3 | ||||
| 2. Round | 29/09/2019 | Lynx FC | - | FCB Magpies | 2:0 | ||||
| 3. Round | 19/10/2019 | FCB Magpies | - | Mons Calpe S.C. | 1:3 | ||||
| 3. Round | 25/10/2019 | Europa Point FC | - | FCB Magpies | 2:3 | ||||
| 4. Round | 04/11/2019 | Boca Gibraltar | - | FCB Magpies | 1:2 | ||||
| 4. Round | 23/11/2019 | FCB Magpies | - | Lincoln Red Imps | 0:3 | ||||
| 5. Round | 07/12/2019 | FCB Magpies | - | St. Joseph's FC | 0:3 |  |
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| 5. Round | 12/12/2019 | Manchester 62 FC | - | FCB Magpies | 0:2 |
Gibraltar