| 2. Round | 18/09/2020 | Tottenham Hotspur U23 | - | West Ham United U23 | 3:0 | ||||
| 14. Round | 15/01/2021 | Brighton & Hove Albion U23 | - | Tottenham Hotspur U23 | 1:5 | ||||
| 15. Round | 22/01/2021 | West Ham United U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 16. Round | 29/01/2021 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 1:1 | ||||
| 17. Round | 07/02/2021 | Southampton FC U23 | - | Tottenham Hotspur U23 | 1:1 | ||||
| 20. Round | 26/02/2021 | Tottenham Hotspur U23 | - | Blackburn Rovers U23 | 1:1 | ||||
| 18. Round | 05/03/2021 | Tottenham Hotspur U23 | - | Everton FC U23 | 2:1 | ||||
| 21. Round | 15/03/2021 | Derby County U23 | - | Tottenham Hotspur U23 | 1:0 | ||||
| 22. Round | 19/03/2021 | Tottenham Hotspur U23 | - | Manchester United U23 | 3:0 | ||||
| 23. Round | 12/04/2021 | Leicester City U23 | - | Tottenham Hotspur U23 | 1:3 | ||||
| 24. Round | 18/04/2021 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 1:4 | ||||
| 25. Round | 23/04/2021 | Tottenham Hotspur U23 | - | Liverpool FC U23 | 4:1 |
England