| 2. Round | 18/08/2019 | Wolverhampton Wanderers U23 | - | Everton FC U23 | 0:0 |  |
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| 3. Round | 23/08/2019 | Blackburn Rovers U23 | - | Wolverhampton Wanderers U23 | 1:2 | ||||
| 4. Round | 30/08/2019 | Wolverhampton Wanderers U23 | - | Leicester City U23 | 0:2 | ||||
| 5. Round | 14/09/2019 | Manchester City U23 | - | Wolverhampton Wanderers U23 | 1:2 | ||||
| 6. Round | 20/09/2019 | Wolverhampton Wanderers U23 | - | Arsenal FC U23 | 2:2 | ||||
| 7. Round | 27/09/2019 | Wolverhampton Wanderers U23 | - | Southampton FC U23 | 1:2 | ||||
| 8. Round | 20/10/2019 | Liverpool FC U23 | - | Wolverhampton Wanderers U23 | 4:3 | |
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| 9. Round | 26/10/2019 | Wolverhampton Wanderers U23 | - | Tottenham Hotspur U23 | 1:2 | |
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| 10. Round | 01/11/2019 | Derby County U23 | - | Wolverhampton Wanderers U23 | 2:2 | |
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| 11. Round | 23/11/2019 | Wolverhampton Wanderers U23 | - | Chelsea FC U23 | 1:1 | |
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| 13. Round | 16/12/2019 | Everton FC U23 | - | Wolverhampton Wanderers U23 | 3:2 |
England