| 1. Round | 11/08/2023 | Arsenal FC U21 | - | West Ham United U21 | 3:0 | ||||
| 2. Round | 18/08/2023 | West Ham United U21 | - | Sunderland AFC U21 | 2:0 | ||||
| 3. Round | 25/08/2023 | Leeds United U21 | - | West Ham United U21 | 2:5 |  |
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| 4. Round | 01/09/2023 | West Ham United U21 | - | Everton FC U21 | 3:1 | ||||
| 5. Round | 22/09/2023 | West Ham United U21 | - | Southampton FC U21 | 3:3 | ||||
| 6. Round | 30/09/2023 | Manchester City U21 | - | West Ham United U21 | 2:2 | ||||
| 7. Round | 27/10/2023 | West Ham United U21 | - | Middlesbrough FC U21 | 5:0 | ||||
| 8. Round | 04/11/2023 | Liverpool FC U21 | - | West Ham United U21 | 0:4 | ||||
| 9. Round | 01/12/2023 | West Ham United U21 | - | Nottingham Forest U21 | 3:1 | ||||
| 10. Round | 18/12/2023 | Crystal Palace U21 | - | West Ham United U21 | 1:5 | ||||
| 12. Round | 26/01/2024 | West Ham United U21 | - | Stoke City U21 | 3:1 | ||||
| 13. Round | 09/02/2024 | West Ham United U21 | - | Chelsea FC U21 | 0:2 | ||||
| 14. Round | 17/02/2024 | Tottenham Hotspur U21 | - | West Ham United U21 | 1:1 | ||||
| 15. Round | 02/03/2024 | Blackburn Rovers U21 | - | West Ham United U21 | 1:3 |
England