| 1. Round | 12/08/2023 | Manchester City U21 | - | Tottenham Hotspur U21 | 0:5 | ||||
| 4. Round | 02/09/2023 | Tottenham Hotspur U21 | - | Blackburn Rovers U21 | 4:0 | ||||
| 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 | ||||
| 8. Round | 03/11/2023 | Norwich City U21 | - | Tottenham Hotspur U21 | 3:4 | ||||
| 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 |
England