| 5. Ronde | 25.09.2023 | Stoke City U21 | - | Tottenham Hotspur U21 | 0:2 | ||||
| 6. Ronde | 02.10.2023 | Tottenham Hotspur U21 | - | Chelsea FC U21 | 4:2 | ||||
| 7. Ronde | 27.10.2023 | Sunderland AFC U21 | - | Tottenham Hotspur U21 | 2:4 |  |
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| 12. Ronde | 27.01.2024 | Tottenham Hotspur U21 | - | Aston Villa U21 | 5:3 | ||||
| 14. Ronde | 17.02.2024 | Tottenham Hotspur U21 | - | West Ham United U21 | 1:1 | ||||
| 15. Ronde | 02.03.2024 | Tottenham Hotspur U21 | - | Everton FC U21 | 1:2 | ||||
| 16. Ronde | 08.03.2024 | Arsenal FC U21 | - | Tottenham Hotspur U21 | 1:1 | ||||
| 17. Ronde | 17.03.2024 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 | ||||
| 18. Ronde | 06.04.2024 | Tottenham Hotspur U21 | - | Reading FC U21 | 2:2 | ||||
| 19. Ronde | 15.04.2024 | Tottenham Hotspur U21 | - | Wolverhampton Wanderers U21 | 5:1 | ||||
| 9. Ronde | 20.04.2024 | Tottenham Hotspur U21 | - | Manchester United U21 | 2:2 | |
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| 20. Ronde | 26.04.2024 | Fulham FC U21 | - | Tottenham Hotspur U21 | 0:2 |
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