| 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 | ||||
| 6. Round | 02/10/2021 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 2:1 |  |
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| 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 | ||||
| 12. Round | 18/12/2021 | Middlesbrough FC [U18] | - | Leeds United [U18] | 2:2 | ||||
| 16. Round | 05/02/2022 | Stoke City [U18] | - | Middlesbrough FC [U18] | 1:2 |  |
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| 13. Round | 22/02/2022 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 0:1 | |
England