| 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 | ||||
| 9. Round | 21/11/2020 | Burnley FC [U18] | - | Middlesbrough FC [U18] | 0:0 | ||||
| 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 | ||||
| 18. Round | 20/02/2021 | Manchester City [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 19. Round | 27/03/2021 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 1:3 | ||||
| 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 | ||||
| 25. Round | 01/05/2021 | Middlesbrough FC [U18] | - | Stoke City [U18] | 3:1 |
Kenya
Germany