| 2. Round | 13/09/2019 | Glacis United FC | - | Mons Calpe S.C. | 0:5 | ||||
| 2. Round | 22/09/2019 | Europa Point FC | - | Glacis United FC | 0:3 |  |
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| 3. Round | 26/10/2019 | Glacis United FC | - | Manchester 62 FC | 2:3 |  |
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| 4. Round | 22/11/2019 | Glacis United FC | - | College 1975 FC | 4:0 | |
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| 4. Round | 29/11/2019 | Europa FC | - | Glacis United FC | 6:2 | |
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| 5. Round | 05/12/2019 | Glacis United FC | - | Boca Gibraltar | 0:2 | ||||
| 5. Round | 10/12/2019 | Glacis United FC | - | Lions Gibraltar | 1:3 | |
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Italy