| 5. Round | 25/09/2023 | Stoke City U21 | - | Tottenham Hotspur U21 | 0:2 | ||||
| 6. Round | 02/10/2023 | Tottenham Hotspur U21 | - | Chelsea FC U21 | 4:2 | ||||
| 7. Round | 27/10/2023 | Sunderland AFC U21 | - | Tottenham Hotspur U21 | 2:4 |  |
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| 12. Round | 27/01/2024 | Tottenham Hotspur U21 | - | Aston Villa U21 | 5:3 | ||||
| 14. Round | 17/02/2024 | Tottenham Hotspur U21 | - | West Ham United U21 | 1:1 | ||||
| 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 | |
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| 20. Round | 26/04/2024 | Fulham FC U21 | - | Tottenham Hotspur U21 | 0:2 |
England