| 2. Round | 29/09/2019 | Boca Gibraltar | - | Mons Calpe S.C. | 1:1 | ||||
| 3. Round | 19/10/2019 | Boca Gibraltar | - | Europa Point FC | 1:1 | ||||
| 4. Round | 04/11/2019 | Boca Gibraltar | - | FCB Magpies | 1:2 | ||||
| 4. Round | 23/11/2019 | Europa FC | - | Boca Gibraltar | 6:1 | ||||
| 4. Round | 27/11/2019 | Boca Gibraltar | - | Lincoln Red Imps | 1:8 |  |
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| 5. Round | 05/12/2019 | Glacis United FC | - | Boca Gibraltar | 0:2 |  |
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| 5. Round | 17/12/2019 | Lions Gibraltar | - | Boca Gibraltar | 6:4 | |
Spain