| 1. Round | 10/08/2024 | Middlesbrough FC | - | Swansea City | 1:0 |  |
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| 2. Round | 17/08/2024 | Derby County | - | Middlesbrough FC | 1:0 | ||||
| 3. Round | 24/08/2024 | Middlesbrough FC | - | Portsmouth FC | 2:2 | ||||
| 23. Round | 26/12/2024 | Middlesbrough FC | - | Sheffield Wednesday | 3:3 | ||||
| 24. Round | 29/12/2024 | Middlesbrough FC | - | Burnley FC | 0:0 | ||||
| 25. Round | 01/01/2025 | Hull City | - | Middlesbrough FC | 0:1 | ||||
| 26. Round | 04/01/2025 | Middlesbrough FC | - | Cardiff City | 1:1 | ||||
| 27. Round | 18/01/2025 | Portsmouth FC | - | Middlesbrough FC | 2:1 | ||||
| 28. Round | 21/01/2025 | Middlesbrough FC | - | West Bromwich Albion | 2:0 |
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