| 1. Round | 12/09/2020 | West Ham United [U18] | - | Tottenham Hotspur [U18] | 1:4 | ||||
| 3. Round | 26/09/2020 | West Ham United [U18] | - | Fulham FC [U18] | 1:2 | ||||
| 9. Round | 21/11/2020 | Reading FC [U18] | - | West Ham United [U18] | 1:2 | ||||
| 10. Round | 28/11/2020 | West Bromwich Albion [U18] | - | West Ham United [U18] | 2:2 | ||||
| 11. Round | 12/12/2020 | West Ham United [U18] | - | Norwich City [U18] | 0:3 | ||||
| 14. Round | 20/04/2021 | Tottenham Hotspur [U18] | - | West Ham United [U18] | 1:1 | ||||
| 24. Round | 24/04/2021 | Norwich City [U18] | - | West Ham United [U18] | 3:3 |  |
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| 25. Round | 01/05/2021 | West Ham United [U18] | - | Southampton FC [U18] | 3:2 | ||||
| 26. Round | 08/05/2021 | Leicester City [U18] | - | West Ham United [U18] | 1:1 |
Bermuda