| 8. Round | 20/10/2018 | West Ham United [U18] | - | Chelsea FC [U18] | 0:5 | ||||
| 10. Round | 24/11/2018 | Reading FC [U18] | - | West Ham United [U18] | 0:2 | ||||
| 11. Round | 15/12/2018 | West Ham United [U18] | - | Brighton & Hove Albion [U18] | 2:2 | ||||
| 12. Round | 05/01/2019 | Southampton FC [U18] | - | West Ham United [U18] | 5:1 | ||||
| 13. Round | 12/01/2019 | West Ham United [U18] | - | Norwich City [U18] | 2:0 | ||||
| 14. Round | 19/01/2019 | West Ham United [U18] | - | Swansea City [U18] | 2:0 | ||||
| 16. Round | 23/02/2019 | West Ham United [U18] | - | Aston Villa [U18] | 3:1 | ||||
| 15. Round | 09/03/2019 | Fulham FC [U18] | - | West Ham United [U18] | 2:0 | ||||
| 18. Round | 16/03/2019 | West Ham United [U18] | - | Arsenal FC [U18] | 2:5 | ||||
| 22. Round | 27/04/2019 | Brighton & Hove Albion [U18] | - | West Ham United [U18] | 3:1 |  |
England