| 22. Ronde | 16.12.2023 | Swansea City | - | Middlesbrough FC | 1:2 | ||||
| 23. Ronde | 23.12.2023 | Middlesbrough FC | - | West Bromwich Albion | 1:0 | ||||
| 24. Ronde | 26.12.2023 | Rotherham United | - | Middlesbrough FC | 1:0 | ||||
| 25. Ronde | 29.12.2023 | Huddersfield Town | - | Middlesbrough FC | 1:2 | ||||
| 26. Ronde | 01.01.2024 | Middlesbrough FC | - | Coventry City | 1:3 | ||||
| 27. Ronde | 13.01.2024 | Millwall FC | - | Middlesbrough FC | 1:3 | ||||
| 28. Ronde | 20.01.2024 | Middlesbrough FC | - | Rotherham United | 1:1 | ||||
| 30. Ronde | 04.02.2024 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
| 31. Ronde | 10.02.2024 | Middlesbrough FC | - | Bristol City | 1:2 | ||||
| 32. Ronde | 14.02.2024 | Preston North End | - | Middlesbrough FC | 2:1 | ||||
| 33. Ronde | 17.02.2024 | Leicester City | - | Middlesbrough FC | 1:2 |  |
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| 34. Ronde | 24.02.2024 | Middlesbrough FC | - | Plymouth Argyle | 0:2 |
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