| 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 | ||||
| 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 | |
|||
| 10. Round | 01/11/2019 | Derby County U23 | - | Wolverhampton Wanderers U23 | 2:2 | ||||
| 11. Round | 23/11/2019 | Wolverhampton Wanderers U23 | - | Chelsea FC U23 | 1:1 | ||||
| 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 | |
England