| 24. Round | 19/08/2023 | Middlesbrough FC [U18] | - | Nottingham Forest [U18] | 1:1 | ||||
| 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 | ||||
| 14. Round | 13/01/2024 | Derby County [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 2. Round | 27/04/2024 | Nottingham Forest [U18] | - | Middlesbrough FC [U18] | 1:0 | ||||
| 25. Round | 04/05/2024 | Sunderland AFC [U18] | - | Middlesbrough FC [U18] | 2:4 |
England