| 1. Round | 14/01/2020 | Boca Gibraltar | - | Europa Point FC | 2:4 |  |
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| 2. Round | 23/01/2020 | College 1975 FC | - | Europa Point FC | 2:6 | |
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| 3. Round | 30/01/2020 | Europa Point FC | - | Glacis United FC | 2:1 | ||||
| 6. Round | 25/02/2020 | Europa Point FC | - | Boca Gibraltar | 2:1 | ||||
| 7. Round | 10/03/2020 | Europa Point FC | - | College 1975 FC | 5:5 |  |
England