| 1. Ronde | 12.08.2023 | Middlesbrough FC [U18] | - | Manchester United [U18] | 0:4 | ||||
| 4. Ronde | 16.09.2023 | Middlesbrough FC [U18] | - | Manchester City [U18] | 0:6 | ||||
| 5. Ronde | 23.09.2023 | Wolverhampton Wanderers [U18] | - | Middlesbrough FC [U18] | 1:2 |  |
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| 6. Ronde | 30.09.2023 | Leeds United [U18] | - | Middlesbrough FC [U18] | 2:4 | |
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| 8. Ronde | 28.10.2023 | Middlesbrough FC [U18] | - | Stoke City [U18] | 0:2 | ||||
| 9. Ronde | 04.11.2023 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 3:1 | ||||
| 10. Ronde | 17.11.2023 | Middlesbrough FC [U18] | - | Derby County [U18] | 2:2 |
Engeland