| 3. Round | 27/08/2022 | Sunderland AFC [U18] | - | Middlesbrough FC [U18] | 6:3 | ||||
| 18. Round | 11/02/2023 | Manchester City [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 19. Round | 18/02/2023 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 0:2 | ||||
| 16. Round | 28/02/2023 | Leeds United [U18] | - | Middlesbrough FC [U18] | 2:2 | ||||
| 11. Round | 25/03/2023 | Middlesbrough FC [U18] | - | Stoke City [U18] | 1:1 | ||||
| 23. Round | 01/04/2023 | Blackburn Rovers [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 4. Round | 08/04/2023 | Middlesbrough FC [U18] | - | Manchester City [U18] | 1:2 | ||||
| 24. Round | 15/04/2023 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 0:2 |  |
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| 14. Round | 18/04/2023 | Everton FC [U18] | - | Middlesbrough FC [U18] | 3:0 | ||||
| 25. Round | 21/04/2023 | Middlesbrough FC [U18] | - | Manchester United [U18] | 0:2 | ||||
| 26. Round | 29/04/2023 | Middlesbrough FC [U18] | - | Wolverhampton Wanderers [U18] | 2:1 | ||||
| 10. Round | 05/05/2023 | Derby County [U18] | - | Middlesbrough FC [U18] | 3:0 |
Belgium