| 1. Ronde | 12.08.2019 | Brighton & Hove Albion U23 | - | Wolverhampton Wanderers U23 | 2:0 |  |
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| 2. Ronde | 18.08.2019 | Wolverhampton Wanderers U23 | - | Everton FC U23 | 0:0 | ||||
| 4. Ronde | 30.08.2019 | Wolverhampton Wanderers U23 | - | Leicester City U23 | 0:2 | |
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| 5. Ronde | 14.09.2019 | Manchester City U23 | - | Wolverhampton Wanderers U23 | 1:2 | ||||
| 6. Ronde | 20.09.2019 | Wolverhampton Wanderers U23 | - | Arsenal FC U23 | 2:2 | ||||
| 7. Ronde | 27.09.2019 | Wolverhampton Wanderers U23 | - | Southampton FC U23 | 1:2 | ||||
| 8. Ronde | 20.10.2019 | Liverpool FC U23 | - | Wolverhampton Wanderers U23 | 4:3 | ||||
| 9. Ronde | 26.10.2019 | Wolverhampton Wanderers U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 11. Ronde | 23.11.2019 | Wolverhampton Wanderers U23 | - | Chelsea FC U23 | 1:1 | ||||
| 12. Ronde | 09.12.2019 | Wolverhampton Wanderers U23 | - | Brighton & Hove Albion U23 | 1:1 | ||||
| 13. Ronde | 16.12.2019 | Everton FC U23 | - | Wolverhampton Wanderers U23 | 3:2 |  |
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| 14. Ronde | 03.01.2020 | Leicester City U23 | - | Wolverhampton Wanderers U23 | 5:1 | ||||
| 15. Ronde | 10.01.2020 | Wolverhampton Wanderers U23 | - | Blackburn Rovers U23 | 0:1 |
Engeland