| 2. Round | 17/08/2019 | Chelsea FC [U18] | - | West Ham United [U18] | 4:3 | ||||
| 4. Round | 31/08/2019 | Reading FC [U18] | - | West Ham United [U18] | 3:3 | ||||
| 6. Round | 21/09/2019 | West Ham United [U18] | - | Norwich City [U18] | 4:1 | ||||
| 7. Round | 05/10/2019 | Fulham FC [U18] | - | West Ham United [U18] | 5:1 | ||||
| 8. Round | 19/10/2019 | West Ham United [U18] | - | Brighton & Hove Albion [U18] | 1:1 | ||||
| 12. Round | 02/11/2019 | Swansea City [U18] | - | West Ham United [U18] | 2:8 | ||||
| 9. Round | 09/11/2019 | Leicester City [U18] | - | West Ham United [U18] | 1:3 | ||||
| 11. Round | 07/12/2019 | Southampton FC [U18] | - | West Ham United [U18] | 0:5 | ||||
| 13. Round | 11/01/2020 | West Ham United [U18] | - | Chelsea FC [U18] | 2:1 | ||||
| 15. Round | 01/02/2020 | Arsenal FC [U18] | - | West Ham United [U18] | 1:5 | ||||
| 16. Round | 22/02/2020 | West Ham United [U18] | - | Tottenham Hotspur [U18] | 3:1 |
England