| 2. Round | 20/03/2021 | Glacis United FC | - | College 1975 FC | 4:1 |  |
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| 4. Round | 03/04/2021 | Manchester 62 FC | - | College 1975 FC | 3:3 | ||||
| 5. Round | 09/04/2021 | College 1975 FC | - | FCB Magpies | 1:8 | ||||
| 6. Round | 18/04/2021 | Europa Point FC | - | College 1975 FC | 0:6 | ||||
| 10. Round | 22/04/2021 | FCB Magpies | - | College 1975 FC | 3:0 |
Gibraltar