| 2. Round | 17/08/2019 | Wolverhampton Wanderers [U18] | - | Manchester United [U18] | 2:0 | ||||
| 3. Round | 24/08/2019 | Wolverhampton Wanderers [U18] | - | Liverpool FC [U18] | 1:1 | ||||
| 4. Round | 31/08/2019 | Sunderland AFC [U18] | - | Wolverhampton Wanderers [U18] | 0:2 | ||||
| 5. Round | 14/09/2019 | Middlesbrough FC [U18] | - | Wolverhampton Wanderers [U18] | 2:0 | ||||
| 6. Round | 21/09/2019 | Wolverhampton Wanderers [U18] | - | West Bromwich Albion [U18] | 4:2 | ||||
| 7. Round | 05/10/2019 | Manchester City [U18] | - | Wolverhampton Wanderers [U18] | 2:0 | ||||
| 8. Round | 19/10/2019 | Wolverhampton Wanderers [U18] | - | Everton FC [U18] | 0:3 | ||||
| 9. Round | 09/11/2019 | Derby County [U18] | - | Wolverhampton Wanderers [U18] | 5:0 | ||||
| 10. Round | 30/11/2019 | Newcastle United [U18] | - | Wolverhampton Wanderers [U18] | 0:2 |  |
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| 11. Round | 07/12/2019 | Wolverhampton Wanderers [U18] | - | Blackburn Rovers [U18] | 0:3 | ||||
| 12. Round | 04/01/2020 | Wolverhampton Wanderers [U18] | - | Stoke City [U18] | 1:3 |
Spain