| 1. Round | 13/08/2019 | Manchester 62 FC | - | Boca Gibraltar | 0:0 | ||||
| 3. Round | 26/10/2019 | Glacis United FC | - | Manchester 62 FC | 2:3 | ||||
| 3. Round | 31/10/2019 | Manchester 62 FC | - | Lions Gibraltar | 0:3 |  |
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| 4. Round | 21/11/2019 | Lynx FC | - | Manchester 62 FC | 5:0 | ||||
| 4. Round | 30/11/2019 | Manchester 62 FC | - | Mons Calpe S.C. | 1:4 | ||||
| 5. Round | 07/12/2019 | Europa Point FC | - | Manchester 62 FC | 1:3 |  |
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| 5. Round | 12/12/2019 | Manchester 62 FC | - | FCB Magpies | 0:2 | |
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| 5. Round | 19/12/2019 | Lincoln Red Imps | - | Manchester 62 FC | 2:0 |
Gibraltar