| 17. Round | 28/01/2023 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 4:2 | ||||
| 19. Round | 18/02/2023 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 0:2 | ||||
| 20. Round | 25/02/2023 | Stoke City [U18] | - | Middlesbrough FC [U18] | 3:0 | ||||
| 23. Round | 01/04/2023 | Blackburn Rovers [U18] | - | Middlesbrough FC [U18] | 4:1 |  |
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| 24. Round | 15/04/2023 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 0:2 | ||||
| 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 |
England