| 13. Round | 13/11/2020 | Middlesbrough FC [U18] | - | Manchester United [U18] | 1:4 | ||||
| 10. Round | 28/11/2020 | Wolverhampton Wanderers [U18] | - | Middlesbrough FC [U18] | 2:1 | ||||
| 14. Round | 30/01/2021 | Middlesbrough FC [U18] | - | Leeds United [U18] | 5:2 | ||||
| 15. Round | 06/03/2021 | Derby County [U18] | - | Middlesbrough FC [U18] | 1:2 | ||||
| 20. Round | 13/03/2021 | Everton FC [U18] | - | Middlesbrough FC [U18] | 2:1 | ||||
| 12. Round | 16/03/2021 | Stoke City [U18] | - | Middlesbrough FC [U18] | 1:1 | ||||
| 16. Round | 07/04/2021 | Sunderland AFC [U18] | - | Middlesbrough FC [U18] | 0:3 | ||||
| 23. Round | 17/04/2021 | Middlesbrough FC [U18] | - | Wolverhampton Wanderers [U18] | 2:1 | ||||
| 17. Round | 21/04/2021 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 3:1 | ||||
| 22. Round | 27/04/2021 | Middlesbrough FC [U18] | - | Burnley FC [U18] | 4:1 |  |
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| 25. Round | 01/05/2021 | Middlesbrough FC [U18] | - | Stoke City [U18] | 3:1 | ||||
| 26. Round | 08/05/2021 | Manchester United [U18] | - | Middlesbrough FC [U18] | 8:1 |
England