| 4. Round | 16/09/2023 | Tottenham Hotspur [U18] | - | Brighton & Hove Albion [U18] | 4:2 | ||||
| 5. Round | 23/09/2023 | Tottenham Hotspur [U18] | - | Reading FC [U18] | 3:0 | ||||
| 6. Round | 30/09/2023 | West Bromwich Albion [U18] | - | Tottenham Hotspur [U18] | 1:2 | ||||
| 8. Round | 28/10/2023 | Chelsea FC [U18] | - | Tottenham Hotspur [U18] | 3:4 | ||||
| 9. Round | 04/11/2023 | Tottenham Hotspur [U18] | - | Crystal Palace [U18] | 2:5 | ||||
| 14. Round | 12/01/2024 | Tottenham Hotspur [U18] | - | Aston Villa [U18] | 3:2 | ||||
| 13. Round | 02/02/2024 | Southampton FC [U18] | - | Tottenham Hotspur [U18] | 3:6 | ||||
| 21. Round | 06/04/2024 | Reading FC [U18] | - | Tottenham Hotspur [U18] | 1:6 |  |
|||
| 18. Round | 16/04/2024 | Norwich City [U18] | - | Tottenham Hotspur [U18] | 2:0 | ||||
| 24. Round | 27/04/2024 | Tottenham Hotspur [U18] | - | West Bromwich Albion [U18] | 5:3 |
England