| 17. Ronde | 17.02.2024 | Middlesbrough FC [U18] | - | Leeds United [U18] | 1:1 |  |
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| 18. Ronde | 24.02.2024 | Manchester United [U18] | - | Middlesbrough FC [U18] | 3:0 | ||||
| 19. Ronde | 09.03.2024 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 2:2 | |
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| 21. Ronde | 06.04.2024 | Stoke City [U18] | - | Middlesbrough FC [U18] | 1:1 | ||||
| 23. Ronde | 20.04.2024 | Manchester City [U18] | - | Middlesbrough FC [U18] | 2:1 | ||||
| 2. Ronde | 27.04.2024 | Nottingham Forest [U18] | - | Middlesbrough FC [U18] | 1:0 | ||||
| 22. Ronde | 30.04.2024 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 1:2 | ||||
| 25. Ronde | 04.05.2024 | Sunderland AFC [U18] | - | Middlesbrough FC [U18] | 2:4 | ||||
| 26. Ronde | 07.05.2024 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 3:4 | |
Engeland