| 1. Round | 14/08/2019 | Lions Gibraltar | - | Europa Point FC | 0:0 | ||||
| 2. Round | 15/09/2019 | Europa FC | - | Europa Point FC | 1:0 | ||||
| 2. Round | 22/09/2019 | Europa Point FC | - | Glacis United FC | 0:3 |  |
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| 3. Round | 05/10/2019 | Mons Calpe S.C. | - | Europa Point FC | 0:2 | ||||
| 3. Round | 19/10/2019 | Boca Gibraltar | - | Europa Point FC | 1:1 | |
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| 4. Round | 03/11/2019 | Lincoln Red Imps | - | Europa Point FC | 3:0 | ||||
| 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