| 1. Round | 12/08/2023 | Aston Villa [U18] | - | Tottenham Hotspur [U18] | 4:0 |  |
|||
| 3. Round | 26/08/2023 | Arsenal FC [U18] | - | Tottenham Hotspur [U18] | 2:4 | ||||
| 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 | ||||
| 7. Round | 07/10/2023 | Tottenham Hotspur [U18] | - | Norwich City [U18] | 7:2 | ||||
| 9. Round | 04/11/2023 | Tottenham Hotspur [U18] | - | Crystal Palace [U18] | 2:5 | |
|||
| 10. Round | 11/11/2023 | Leicester City [U18] | - | Tottenham Hotspur [U18] | 1:4 | ||||
| 11. Round | 09/12/2023 | Fulham FC [U18] | - | Tottenham Hotspur [U18] | 1:3 |  |
|||
| 12. Round | 16/12/2023 | Tottenham Hotspur [U18] | - | West Ham United [U18] | 2:4 | ||||
| 14. Round | 12/01/2024 | Tottenham Hotspur [U18] | - | Aston Villa [U18] | 3:2 | ||||
| 15. Round | 27/01/2024 | Brighton & Hove Albion [U18] | - | Tottenham Hotspur [U18] | 2:2 | ||||
| 13. Round | 02/02/2024 | Southampton FC [U18] | - | Tottenham Hotspur [U18] | 3:6 | ||||
| 16. Round | 10/02/2024 | Tottenham Hotspur [U18] | - | Leicester City [U18] | 3:4 | ||||
| 17. Round | 17/02/2024 | Tottenham Hotspur [U18] | - | Chelsea FC [U18] | 1:4 |
England