| 1. Round | 14/08/2023 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 2. Round | 18/08/2023 | Middlesbrough FC U21 | - | Everton FC U21 | 2:2 | ||||
| 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 | ||||
| 5. Round | 25/09/2023 | Leicester City U21 | - | Middlesbrough FC U21 | 1:3 |  |
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| 6. Round | 29/09/2023 | Middlesbrough FC U21 | - | Stoke City U21 | 4:1 | |
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| 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 | ||||
| 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 | |
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| 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 | ||||
| 18. Round | 08/04/2024 | Fulham FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 20. Round | 26/04/2024 | Middlesbrough FC U21 | - | Crystal Palace U21 | 2:3 |
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