| 4. Round | 02/09/2023 | Tottenham Hotspur U21 | - | Blackburn Rovers U21 | 4:0 | ||||
| 7. Round | 27/10/2023 | Sunderland AFC U21 | - | Tottenham Hotspur U21 | 2:4 | ||||
| 8. Round | 03/11/2023 | Norwich City U21 | - | Tottenham Hotspur U21 | 3:4 | ||||
| 15. Round | 02/03/2024 | Tottenham Hotspur U21 | - | Everton FC U21 | 1:2 | ||||
| 16. Round | 08/03/2024 | Arsenal FC U21 | - | Tottenham Hotspur U21 | 1:1 | ||||
| 17. Round | 17/03/2024 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 | ||||
| 18. Round | 06/04/2024 | Tottenham Hotspur U21 | - | Reading FC U21 | 2:2 | ||||
| 19. Round | 15/04/2024 | Tottenham Hotspur U21 | - | Wolverhampton Wanderers U21 | 5:1 | ||||
| 9. Round | 20/04/2024 | Tottenham Hotspur U21 | - | Manchester United U21 | 2:2 | ||||
| 20. Round | 26/04/2024 | Fulham FC U21 | - | Tottenham Hotspur U21 | 0:2 | ||||
| 13. Round | 29/04/2024 | Crystal Palace U21 | - | Tottenham Hotspur U21 | 5:0 |
England