| 1. Round | 10/08/2019 | Everton FC [U18] | - | Derby County [U18] | 2:1 | ||||
| 3. Round | 24/08/2019 | Newcastle United [U18] | - | Derby County [U18] | 2:1 | ||||
| 4. Round | 31/08/2019 | Derby County [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 7. Round | 05/10/2019 | Blackburn Rovers [U18] | - | Derby County [U18] | 0:0 | ||||
| 8. Round | 19/10/2019 | Sunderland AFC [U18] | - | Derby County [U18] | 0:3 | ||||
| 9. Round | 09/11/2019 | Derby County [U18] | - | Wolverhampton Wanderers [U18] | 5:0 | ||||
| 10. Round | 30/11/2019 | Manchester City [U18] | - | Derby County [U18] | 1:0 | ||||
| 11. Round | 07/12/2019 | Derby County [U18] | - | Liverpool FC [U18] | 1:5 | ||||
| 14. Round | 18/01/2020 | Middlesbrough FC [U18] | - | Derby County [U18] | 0:2 |  |
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| 16. Round | 22/02/2020 | Manchester United [U18] | - | Derby County [U18] | 1:2 |
England