| 2. Round | 21/08/2021 | Burnley FC [U18] | - | Middlesbrough FC [U18] | 2:2 | ||||
| 5. Round | 25/09/2021 | Manchester City [U18] | - | Middlesbrough FC [U18] | 2:0 | ||||
| 4. Round | 07/10/2021 | Manchester United [U18] | - | Middlesbrough FC [U18] | 3:3 | ||||
| 9. Round | 06/11/2021 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 3:4 | ||||
| 11. Round | 04/12/2021 | Sunderland AFC [U18] | - | Middlesbrough FC [U18] | 3:4 | ||||
| 15. Round | 22/01/2022 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 2:6 | ||||
| 14. Round | 27/01/2022 | Wolverhampton Wanderers [U18] | - | Middlesbrough FC [U18] | 2:0 | ||||
| 13. Round | 22/02/2022 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 0:1 |
England