| 1. Round | 13/08/2022 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 6:2 | ||||
| 2. Round | 20/08/2022 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 3:2 |  |
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| 5. Round | 17/09/2022 | Nottingham Forest [U18] | - | Middlesbrough FC [U18] | 0:0 | ||||
| 7. Round | 15/10/2022 | Wolverhampton Wanderers [U18] | - | Middlesbrough FC [U18] | 2:3 | ||||
| 13. Round | 17/12/2022 | Manchester United [U18] | - | Middlesbrough FC [U18] | 3:0 | ||||
| 12. Round | 21/12/2022 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 4:2 | ||||
| 17. Round | 28/01/2023 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 4:2 | |
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| 18. Round | 11/02/2023 | Manchester City [U18] | - | Middlesbrough FC [U18] | 4:1 | |
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| 16. Round | 28/02/2023 | Leeds United [U18] | - | Middlesbrough FC [U18] | 2:2 | |
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| 22. Round | 18/03/2023 | Middlesbrough FC [U18] | - | Derby County [U18] | 1:0 | |
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| 11. Round | 25/03/2023 | Middlesbrough FC [U18] | - | Stoke City [U18] | 1:1 | |
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| 23. Round | 01/04/2023 | Blackburn Rovers [U18] | - | Middlesbrough FC [U18] | 4:1 |  |
England