| 7. Round | 05/10/2019 | Tottenham Hotspur [U18] | - | Aston Villa [U18] | 2:4 |  |
|||
| 8. Round | 19/10/2019 | Arsenal FC [U18] | - | Tottenham Hotspur [U18] | 2:2 |  |
|||
| 11. Round | 07/12/2019 | Tottenham Hotspur [U18] | - | Reading FC [U18] | 2:3 | ||||
| 10. Round | 21/12/2019 | Leicester City [U18] | - | Tottenham Hotspur [U18] | 3:4 | |
|||
| 12. Round | 04/01/2020 | Tottenham Hotspur [U18] | - | Fulham FC [U18] | 4:1 | ||||
| 13. Round | 11/01/2020 | Brighton & Hove Albion [U18] | - | Tottenham Hotspur [U18] | 0:1 | |
|
||
| 14. Round | 18/01/2020 | Tottenham Hotspur [U18] | - | Swansea City [U18] | 3:0 | |
|||
| 15. Round | 01/02/2020 | Norwich City [U18] | - | Tottenham Hotspur [U18] | 1:1 | |
|||
| 16. Round | 22/02/2020 | West Ham United [U18] | - | Tottenham Hotspur [U18] | 3:1 | ||||
| 17. Round | 29/02/2020 | Tottenham Hotspur [U18] | - | Southampton FC [U18] | 6:1 | |
England