| 4. Round | 01/09/2018 | Southampton FC [U18] | - | Tottenham Hotspur [U18] | 2:5 | ||||
| 6. Round | 22/09/2018 | West Ham United [U18] | - | Tottenham Hotspur [U18] | 0:9 | ||||
| 7. Round | 06/10/2018 | Tottenham Hotspur [U18] | - | Norwich City [U18] | 7:0 | ||||
| 10. Round | 24/11/2018 | Tottenham Hotspur [U18] | - | Arsenal FC [U18] | 3:2 | ||||
| 11. Round | 01/12/2018 | Leicester City [U18] | - | Tottenham Hotspur [U18] | 0:4 | ||||
| 16. Round | 23/02/2019 | Reading FC [U18] | - | Tottenham Hotspur [U18] | 0:2 | ||||
| 17. Round | 02/03/2019 | Tottenham Hotspur [U18] | - | West Ham United [U18] | 5:3 | ||||
| 18. Round | 16/03/2019 | Norwich City [U18] | - | Tottenham Hotspur [U18] | 0:3 | ||||
| 15. Round | 24/03/2019 | Tottenham Hotspur [U18] | - | Southampton FC [U18] | 3:1 | ||||
| 19. Round | 30/03/2019 | Tottenham Hotspur [U18] | - | Fulham FC [U18] | 4:0 | ||||
| 21. Round | 02/04/2019 | Arsenal FC [U18] | - | Tottenham Hotspur [U18] | 3:2 | ||||
| 20. Round | 06/04/2019 | Aston Villa [U18] | - | Tottenham Hotspur [U18] | 2:3 | ||||
| 14. Round | 10/04/2019 | Chelsea FC [U18] | - | Tottenham Hotspur [U18] | 0:2 | ||||
| 22. Round | 27/04/2019 | Tottenham Hotspur [U18] | - | Leicester City [U18] | 3:4 |
England