| 1. Round | 14/08/2023 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 2:2 |  |
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| 5. Round | 25/09/2023 | Leicester City U21 | - | Middlesbrough FC U21 | 1:3 | ||||
| 6. Round | 29/09/2023 | Middlesbrough FC U21 | - | Stoke City U21 | 4:1 | |
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| 10. Round | 18/12/2023 | Reading FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 11. Round | 12/01/2024 | Arsenal FC U21 | - | Middlesbrough FC U21 | 1:0 | ||||
| 17. Round | 17/03/2024 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 | ||||
| 19. Round | 15/04/2024 | Sunderland AFC U21 | - | Middlesbrough FC U21 | 1:2 | ||||
| 20. Round | 26/04/2024 | Middlesbrough FC U21 | - | Crystal Palace U21 | 2:3 |
England