| 16. Round | 23/11/2024 | Oxford United | - | Middlesbrough FC | 2:6 | ||||
| 17. Round | 27/11/2024 | Middlesbrough FC | - | Blackburn Rovers | 0:1 | ||||
| 18. Round | 30/11/2024 | Middlesbrough FC | - | Hull City | 3:1 | ||||
| 21. Round | 14/12/2024 | Middlesbrough FC | - | Millwall FC | 1:0 | ||||
| 22. Round | 21/12/2024 | Plymouth Argyle | - | Middlesbrough FC | 3:3 | ||||
| 23. Round | 26/12/2024 | Middlesbrough FC | - | Sheffield Wednesday | 3:3 |
England