| 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 | ||||
| 4. Round | 03/10/2020 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 3:4 | ||||
| 5. Round | 17/10/2020 | Middlesbrough FC [U18] | - | Manchester City [U18] | 0:0 |  |
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| 6. Round | 24/10/2020 | Blackburn Rovers [U18] | - | Middlesbrough FC [U18] | 1:3 | |
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| 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 | |
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| 9. Round | 21/11/2020 | Burnley FC [U18] | - | Middlesbrough FC [U18] | 0:0 | |
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| 11. Round | 12/12/2020 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 1:4 | ||||
| 15. Round | 06/03/2021 | Derby County [U18] | - | Middlesbrough FC [U18] | 1:2 |  |
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| 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 | ||||
| 19. Round | 27/03/2021 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 1:3 |  |
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| 16. Round | 07/04/2021 | Sunderland AFC [U18] | - | Middlesbrough FC [U18] | 0:3 |
Scotland