| 1. Round | 11/08/2023 | Wolverhampton Wanderers U21 | - | Fulham FC U21 | 2:3 |  |
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| 2. Round | 21/08/2023 | Stoke City U21 | - | Wolverhampton Wanderers U21 | 2:1 |  |
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| 3. Round | 25/08/2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 | ||||
| 4. Round | 01/09/2023 | Wolverhampton Wanderers U21 | - | Crystal Palace U21 | 3:2 | ||||
| 5. Round | 24/09/2023 | Liverpool FC U21 | - | Wolverhampton Wanderers U21 | 2:0 | ||||
| 6. Round | 02/10/2023 | Wolverhampton Wanderers U21 | - | Leeds United U21 | 2:0 | |
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| 7. Round | 30/10/2023 | Wolverhampton Wanderers U21 | - | Southampton FC U21 | 2:1 | ||||
| 8. Round | 03/11/2023 | Nottingham Forest U21 | - | Wolverhampton Wanderers U21 | 2:2 | |
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| 9. Round | 04/12/2023 | Leicester City U21 | - | Wolverhampton Wanderers U21 | 1:3 | |
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| 10. Round | 18/12/2023 | Wolverhampton Wanderers U21 | - | Blackburn Rovers U21 | 1:2 | |
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| 13. Round | 11/02/2024 | Manchester City U21 | - | Wolverhampton Wanderers U21 | 3:3 | ||||
| 14. Round | 19/02/2024 | Wolverhampton Wanderers U21 | - | West Bromwich Albion U21 | 3:0 |
Netherlands