| 2. Round | 22/01/2020 | Glacis United FC | - | Boca Gibraltar | 2:2 | ||||
| 3. Round | 30/01/2020 | Europa Point FC | - | Glacis United FC | 2:1 |  |
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| 4. Round | 06/02/2020 | College 1975 FC | - | Glacis United FC | 1:2 |  |
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| 5. Round | 22/02/2020 | Glacis United FC | - | Mons Calpe S.C. | 0:1 |
England