| 1. Round | 14/08/2019 | Lions Gibraltar | - | Europa Point FC | 0:0 | ||||
| 1. Round | 21/08/2019 | Europa Point FC | - | Lynx FC | 0:5 | ||||
| 2. Round | 22/09/2019 | Europa Point FC | - | Glacis United FC | 0:3 | ||||
| 3. Round | 19/10/2019 | Boca Gibraltar | - | Europa Point FC | 1:1 | ||||
| 4. Round | 30/11/2019 | St. Joseph's FC | - | Europa Point FC | 5:0 |  |
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| 5. Round | 07/12/2019 | Europa Point FC | - | Manchester 62 FC | 1:3 | |
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| 5. Round | 16/12/2019 | Europa Point FC | - | College 1975 FC | 6:1 |
Gibraltar