| 1. Round | 13/08/2019 | Manchester 62 FC | - | Boca Gibraltar | 0:0 | ||||
| 2. Round | 14/09/2019 | St. Joseph's FC | - | Boca Gibraltar | 2:0 | ||||
| 2. Round | 19/09/2019 | Boca Gibraltar | - | Lynx FC | 1:3 | ||||
| 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 | ||||
| 3. Round | 24/10/2019 | College 1975 FC | - | Boca Gibraltar | 0:4 | ||||
| 4. Round | 04/11/2019 | Boca Gibraltar | - | FCB Magpies | 1:2 |  |
Germany