| 2. Round | 20/03/2021 | Glacis United FC | - | College 1975 FC | 4:1 | ||||
| 3. Round | 26/03/2021 | Glacis United FC | - | Manchester 62 FC | 4:1 | ||||
| 4. Round | 03/04/2021 | FCB Magpies | - | Glacis United FC | 1:5 | ||||
| 5. Round | 11/04/2021 | Glacis United FC | - | Europa Point FC | 3:1 | ||||
| 9. Round | 07/05/2021 | Glacis United FC | - | FCB Magpies | 4:1 | ||||
| 10. Round | 10/05/2021 | Europa Point FC | - | Glacis United FC | 0:3 |
Gibraltar