| 4. Round | 31/08/2024 | Cardiff City | - | Middlesbrough FC | 0:2 | ||||
| 17. Round | 27/11/2024 | Middlesbrough FC | - | Blackburn Rovers | 0:1 | ||||
| 22. Round | 21/12/2024 | Plymouth Argyle | - | Middlesbrough FC | 3:3 | ||||
| 25. Round | 01/01/2025 | Hull City | - | Middlesbrough FC | 0:1 |  |
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| 26. Round | 04/01/2025 | Middlesbrough FC | - | Cardiff City | 1:1 | ||||
| 27. Round | 18/01/2025 | Portsmouth FC | - | Middlesbrough FC | 2:1 | ||||
| 29. Round | 25/01/2025 | Preston North End | - | Middlesbrough FC | 2:1 |
England