| 1. Round | 16/10/2020 | Glacis United FC | - | Mons Calpe S.C. | 0:1 |  |
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| 2. Round | 24/10/2020 | Lions Gibraltar | - | Glacis United FC | 3:0 | ||||
| 5. Round | 21/11/2020 | Glacis United FC | - | Europa Point FC | 3:0 | |
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| 6. Round | 29/11/2020 | Glacis United FC | - | St. Joseph's FC | 0:5 | ||||
| 7. Round | 05/12/2020 | College 1975 FC | - | Glacis United FC | 1:5 |
Gibraltar