| 3. Round | 26/09/2020 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 4:0 | ||||
| 5. Round | 17/10/2020 | Middlesbrough FC [U18] | - | Manchester City [U18] | 0:0 | ||||
| 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 | ||||
| 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 |
England