| 1. Round | 13/08/2019 | Manchester 62 FC | - | Boca Gibraltar | 0:0 | ||||
| 4. Round | 23/11/2019 | Europa FC | - | Boca Gibraltar | 6:1 |  |
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| 4. Round | 27/11/2019 | Boca Gibraltar | - | Lincoln Red Imps | 1:8 | ||||
| 5. Round | 05/12/2019 | Glacis United FC | - | Boca Gibraltar | 0:2 | ||||
| 5. Round | 17/12/2019 | Lions Gibraltar | - | Boca Gibraltar | 6:4 | |
Gibraltar