| 1. Round | 12/08/2023 | Middlesbrough FC [U18] | - | Manchester United [U18] | 0:4 | ||||
| 4. Round | 16/09/2023 | Middlesbrough FC [U18] | - | Manchester City [U18] | 0:6 | ||||
| 5. Round | 23/09/2023 | Wolverhampton Wanderers [U18] | - | Middlesbrough FC [U18] | 1:2 |  |
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| 6. Round | 30/09/2023 | Leeds United [U18] | - | Middlesbrough FC [U18] | 2:4 | |
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| 8. Round | 28/10/2023 | Middlesbrough FC [U18] | - | Stoke City [U18] | 0:2 | ||||
| 9. Round | 04/11/2023 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 3:1 | ||||
| 10. Round | 17/11/2023 | Middlesbrough FC [U18] | - | Derby County [U18] | 2:2 |
England