| 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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| 8. Round | 12/12/2020 | Glacis United FC | - | FCB Magpies | 0:1 | ||||
| 9. Round | 18/12/2020 | Europa FC | - | Glacis United FC | 1:0 | ||||
| 10. Round | 25/02/2021 | Glacis United FC | - | Lincoln Red Imps | 0:3 |
Gibraltar