| 1. Round | 12/08/2023 | Middlesbrough FC [U18] | - | Manchester United [U18] | 0:4 | ||||
| 3. Round | 26/08/2023 | Middlesbrough FC [U18] | - | Everton FC [U18] | 2:0 |  |
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| 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 | ||||
| 6. Round | 30/09/2023 | Leeds United [U18] | - | Middlesbrough FC [U18] | 2:4 | ||||
| 10. Round | 17/11/2023 | Middlesbrough FC [U18] | - | Derby County [U18] | 2:2 | ||||
| 11. Round | 02/03/2024 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 1:3 | ||||
| 13. Round | 29/03/2024 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 0:2 | ||||
| 23. Round | 20/04/2024 | Manchester City [U18] | - | Middlesbrough FC [U18] | 2:1 | ||||
| 26. Round | 07/05/2024 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 3:4 |
England