| 1. Round | 12/09/2020 | Leeds United [U18] | - | Middlesbrough FC [U18] | 0:3 | ||||
| 2. Round | 19/09/2020 | Middlesbrough FC [U18] | - | Derby County [U18] | 2:3 |  |
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| 4. Round | 03/10/2020 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 3:4 | |
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| 5. Round | 17/10/2020 | Middlesbrough FC [U18] | - | Manchester City [U18] | 0:0 | ||||
| 7. Round | 31/10/2020 | Middlesbrough FC [U18] | - | Everton FC [U18] | 2:0 | ||||
| 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 | ||||
| 18. Round | 20/02/2021 | Manchester City [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 15. Round | 06/03/2021 | Derby County [U18] | - | Middlesbrough FC [U18] | 1:2 | |
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| 12. Round | 16/03/2021 | Stoke City [U18] | - | Middlesbrough FC [U18] | 1:1 | ||||
| 19. Round | 27/03/2021 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 1:3 | |
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| 17. Round | 21/04/2021 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 3:1 | ||||
| 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