| 1. Round | 13/08/2018 | Tottenham Hotspur U23 | - | West Ham United U23 | 1:3 | ||||
| 2. Round | 19/08/2018 | West Ham United U23 | - | Manchester City U23 | 4:6 | ||||
| 3. Round | 24/08/2018 | West Ham United U23 | - | Arsenal FC U23 | 2:3 | ||||
| 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 | ||||
| 11. Round | 26/11/2018 | Blackburn Rovers U23 | - | West Ham United U23 | 1:3 |  |
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| 12. Round | 07/12/2018 | Chelsea FC U23 | - | West Ham United U23 | 3:2 | ||||
| 13. Round | 15/12/2018 | West Ham United U23 | - | Brighton & Hove Albion U23 | 2:4 | ||||
| 14. Round | 05/01/2019 | Manchester City U23 | - | West Ham United U23 | 1:5 | ||||
| 15. Round | 13/01/2019 | West Ham United U23 | - | Tottenham Hotspur U23 | 1:1 | ||||
| 17. Round | 18/02/2019 | West Ham United U23 | - | Liverpool FC U23 | 0:1 | ||||
| 18. Round | 04/03/2019 | West Ham United U23 | - | Blackburn Rovers U23 | 1:3 | ||||
| 22. Round | 29/04/2019 | West Ham United U23 | - | Everton FC U23 | 2:1 |
England