| 1. Round | 11/08/2023 | Arsenal FC U21 | - | West Ham United U21 | 3:0 |  |
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| 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 | ||||
| 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 |
England