| 3. Round | 24/10/2019 | College 1975 FC | - | Boca Gibraltar | 0:4 | ||||
| 4. Round | 01/11/2019 | College 1975 FC | - | Europa FC | 0:12 | ||||
| 4. Round | 22/11/2019 | Glacis United FC | - | College 1975 FC | 4:0 |  |
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| 4. Round | 28/11/2019 | College 1975 FC | - | Lions Gibraltar | 1:6 | |
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| 5. Round | 06/12/2019 | Lynx FC | - | College 1975 FC | 4:0 | |
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| 5. Round | 16/12/2019 | Europa Point FC | - | College 1975 FC | 6:1 |
Spain