| 1. Round | 13/08/2018 | Tottenham Hotspur U23 | - | West Ham United U23 | 1:3 |  |
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| 4. Round | 02/09/2018 | Liverpool FC U23 | - | West Ham United U23 | 1:2 | ||||
| 5. Round | 14/09/2018 | Brighton & Hove Albion U23 | - | West Ham United U23 | 2:1 | ||||
| 7. Round | 01/10/2018 | Everton FC U23 | - | West Ham United U23 | 2:1 | ||||
| 8. Round | 21/10/2018 | West Ham United U23 | - | Swansea City U23 | 5:3 | ||||
| 9. Round | 26/10/2018 | Leicester City U23 | - | West Ham United U23 | 3:0 | ||||
| 10. Round | 03/11/2018 | West Ham United U23 | - | Derby County U23 | 0:2 | ||||
| 12. Round | 07/12/2018 | Chelsea FC U23 | - | West Ham United U23 | 3:2 | ||||
| 14. Round | 05/01/2019 | Manchester City U23 | - | West Ham United U23 | 1:5 | ||||
| 17. Round | 18/02/2019 | West Ham United U23 | - | Liverpool FC U23 | 0:1 | ||||
| 19. Round | 11/03/2019 | Swansea City U23 | - | West Ham United U23 | 0:3 | ||||
| 16. Round | 29/03/2019 | Arsenal FC U23 | - | West Ham United U23 | 1:0 | ||||
| 20. Round | 07/04/2019 | West Ham United U23 | - | Leicester City U23 | 1:0 | ||||
| 21. Round | 15/04/2019 | Derby County U23 | - | West Ham United U23 | 2:2 |
England