| 1. Round | 14/08/2023 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 7. Round | 27/10/2023 | West Ham United U21 | - | Middlesbrough FC U21 | 5:0 | ||||
| 8. Round | 05/11/2023 | Middlesbrough FC U21 | - | Derby County U21 | 1:0 | ||||
| 10. Round | 18/12/2023 | Reading FC U21 | - | Middlesbrough FC U21 | 2:2 |  |
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| 11. Round | 12/01/2024 | Arsenal FC U21 | - | Middlesbrough FC U21 | 1:0 | ||||
| 12. Round | 26/01/2024 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 0:1 | ||||
| 15. Round | 01/03/2024 | Norwich City U21 | - | Middlesbrough FC U21 | 2:3 | ||||
| 16. Round | 08/03/2024 | Middlesbrough FC U21 | - | Manchester United U21 | 3:2 | |
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| 17. Round | 17/03/2024 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 | ||||
| 13. Round | 22/03/2024 | Middlesbrough FC U21 | - | Newcastle United U21 | 3:2 | |
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| 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 |
England