| 1. Round | 10/08/2024 | Middlesbrough FC | - | Swansea City | 1:0 | ||||
| 2. Round | 17/08/2024 | Derby County | - | Middlesbrough FC | 1:0 | ||||
| 3. Round | 24/08/2024 | Middlesbrough FC | - | Portsmouth FC | 2:2 |  |
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| 4. Round | 31/08/2024 | Cardiff City | - | Middlesbrough FC | 0:2 | |
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| 5. Round | 14/09/2024 | Middlesbrough FC | - | Preston North End | 1:1 | ||||
| 6. Round | 21/09/2024 | Sunderland AFC | - | Middlesbrough FC | 1:0 | ||||
| 11. Round | 23/10/2024 | Middlesbrough FC | - | Sheffield United | 1:0 | ||||
| 13. Round | 02/11/2024 | Middlesbrough FC | - | Coventry City | 0:3 | ||||
| 14. Round | 05/11/2024 | Queens Park Rangers | - | Middlesbrough FC | 1:4 | ||||
| 15. Round | 09/11/2024 | Middlesbrough FC | - | Luton Town | 5:1 | ||||
| 16. Round | 23/11/2024 | Oxford United | - | Middlesbrough FC | 2:6 | ||||
| 17. Round | 27/11/2024 | Middlesbrough FC | - | Blackburn Rovers | 0:1 | ||||
| 20. Round | 10/12/2024 | Leeds United | - | Middlesbrough FC | 3:1 | ||||
| 23. Round | 26/12/2024 | Middlesbrough FC | - | Sheffield Wednesday | 3:3 |
England