| 1. Round | 19/10/2020 | College 1975 FC | - | Lincoln Red Imps | 0:8 | ||||
| 3. Round | 02/11/2020 | College 1975 FC | - | Mons Calpe S.C. | 0:6 | ||||
| 5. Round | 23/11/2020 | College 1975 FC | - | Lynx FC | 1:7 | ||||
| 6. Round | 30/11/2020 | Manchester 62 FC | - | College 1975 FC | 3:2 | ||||
| 7. Round | 05/12/2020 | College 1975 FC | - | Glacis United FC | 1:5 | ||||
| 8. Round | 12/12/2020 | St. Joseph's FC | - | College 1975 FC | 13:1 | ||||
| 9. Round | 19/12/2020 | College 1975 FC | - | Europa Point FC | 1:3 | ||||
| 4. Round | 22/02/2021 | Lions Gibraltar | - | College 1975 FC | 3:2 | ||||
| 11. Round | 02/03/2021 | Europa FC | - | College 1975 FC | 9:0 |
Canada