| 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 | ||||
| 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 |  |
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| 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 | ||||
| 9. Round | 26/10/2019 | Wolverhampton Wanderers U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 14. Round | 03/01/2020 | Leicester City U23 | - | Wolverhampton Wanderers U23 | 5:1 |
England