| 1. Round | 12/09/2020 | West Ham United [U18] | - | Tottenham Hotspur [U18] | 1:4 | ||||
| 2. Round | 19/09/2020 | Tottenham Hotspur [U18] | - | Arsenal FC [U18] | 2:0 | ||||
| 3. Round | 26/09/2020 | Brighton & Hove Albion [U18] | - | Tottenham Hotspur [U18] | 1:1 | ||||
| 4. Round | 03/10/2020 | Tottenham Hotspur [U18] | - | Fulham FC [U18] | 3:0 | ||||
| 16. Round | 30/01/2021 | Tottenham Hotspur [U18] | - | Brighton & Hove Albion [U18] | 2:1 | ||||
| 17. Round | 17/02/2021 | Fulham FC [U18] | - | Tottenham Hotspur [U18] | 5:0 | ||||
| 22. Round | 10/04/2021 | Southampton FC [U18] | - | Tottenham Hotspur [U18] | 0:3 | ||||
| 14. Round | 20/04/2021 | Tottenham Hotspur [U18] | - | West Ham United [U18] | 1:1 | ||||
| 24. Round | 24/04/2021 | Tottenham Hotspur [U18] | - | Crystal Palace [U18] | 0:3 | ||||
| 25. Round | 01/05/2021 | West Bromwich Albion [U18] | - | Tottenham Hotspur [U18] | 3:1 | ||||
| 21. Round | 04/05/2021 | Tottenham Hotspur [U18] | - | Norwich City [U18] | 5:2 | ||||
| 26. Round | 08/05/2021 | Tottenham Hotspur [U18] | - | Chelsea FC [U18] | 0:1 | ||||
| 23. Round | 14/05/2021 | Leicester City [U18] | - | Tottenham Hotspur [U18] | 3:1 |
England
Jamaica