| 3. Round | 25/08/2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 |  |
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| 4. Round | 03/09/2023 | Liverpool FC U21 | - | Middlesbrough FC U21 | 1:4 | ||||
| 7. Round | 27/10/2023 | West Ham United U21 | - | Middlesbrough FC U21 | 5:0 | ||||
| 12. Round | 26/01/2024 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 0:1 | ||||
| 9. Round | 23/02/2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | ||||
| 15. Round | 01/03/2024 | Norwich City U21 | - | Middlesbrough FC U21 | 2:3 | |
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| 16. Round | 08/03/2024 | Middlesbrough FC U21 | - | Manchester United U21 | 3:2 | ||||
| 18. Round | 08/04/2024 | Fulham FC U21 | - | Middlesbrough FC U21 | 2:2 | |
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| 19. Round | 15/04/2024 | Sunderland AFC U21 | - | Middlesbrough FC U21 | 1:2 | |
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| 20. Round | 26/04/2024 | Middlesbrough FC U21 | - | Crystal Palace U21 | 2:3 | |
England