| 3. Round | 01/09/2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | ||||
| 4. Round | 23/09/2024 | Leicester City U21 | - | Middlesbrough FC U21 | 3:1 |  |
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| 5. Round | 27/09/2024 | Middlesbrough FC U21 | - | Brighton & Hove Albion U21 | 0:3 | ||||
| 6. Round | 04/10/2024 | Stoke City U21 | - | Middlesbrough FC U21 | 1:3 |  |
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| 7. Round | 25/10/2024 | Middlesbrough FC U21 | - | Aston Villa U21 | 4:2 | |
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| 8. Round | 02/11/2024 | Middlesbrough FC U21 | - | Nottingham Forest U21 | 1:4 | |
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| 10. Round | 13/12/2024 | Norwich City U21 | - | Middlesbrough FC U21 | 1:3 | |
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| 12. Round | 17/01/2025 | Blackburn Rovers U21 | - | Middlesbrough FC U21 | 3:2 | |
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England