| 1. Round | 12/08/2019 | Brighton & Hove Albion U23 | - | Wolverhampton Wanderers U23 | 2:0 | ||||
| 2. Round | 18/08/2019 | Wolverhampton Wanderers U23 | - | Everton FC U23 | 0:0 | ||||
| 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 | ||||
| 9. Round | 26/10/2019 | Wolverhampton Wanderers U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 10. Round | 01/11/2019 | Derby County U23 | - | Wolverhampton Wanderers U23 | 2:2 |  |
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| 12. Round | 09/12/2019 | Wolverhampton Wanderers U23 | - | Brighton & Hove Albion U23 | 1:1 | ||||
| 13. Round | 16/12/2019 | Everton FC U23 | - | Wolverhampton Wanderers U23 | 3:2 | ||||
| 14. Round | 03/01/2020 | Leicester City U23 | - | Wolverhampton Wanderers U23 | 5:1 | ||||
| 15. Round | 10/01/2020 | Wolverhampton Wanderers U23 | - | Blackburn Rovers U23 | 0:1 | ||||
| 16. Round | 03/02/2020 | Southampton FC U23 | - | Wolverhampton Wanderers U23 | 1:0 |
England