| 6. Ronde | 16.09.2023 | Blackburn Rovers | - | Middlesbrough FC | 2:1 | ||||
| 10. Ronde | 03.10.2023 | Middlesbrough FC | - | Cardiff City | 2:0 | ||||
| 11. Ronde | 07.10.2023 | Sunderland AFC | - | Middlesbrough FC | 0:4 | ||||
| 13. Ronde | 24.10.2023 | Norwich City | - | Middlesbrough FC | 1:2 | ||||
| 17. Ronde | 25.11.2023 | Bristol City | - | Middlesbrough FC | 3:2 | ||||
| 18. Ronde | 28.11.2023 | Middlesbrough FC | - | Preston North End | 4:0 |  |
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| 19. Ronde | 02.12.2023 | Leeds United | - | Middlesbrough FC | 3:2 | ||||
| 20. Ronde | 09.12.2023 | Middlesbrough FC | - | Ipswich Town | 0:2 | ||||
| 22. Ronde | 16.12.2023 | Swansea City | - | Middlesbrough FC | 1:2 | ||||
| 24. Ronde | 26.12.2023 | Rotherham United | - | Middlesbrough FC | 1:0 | ||||
| 25. Ronde | 29.12.2023 | Huddersfield Town | - | Middlesbrough FC | 1:2 |  |
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| 26. Ronde | 01.01.2024 | Middlesbrough FC | - | Coventry City | 1:3 | ||||
| 44. Ronde | 22.04.2024 | Middlesbrough FC | - | Leeds United | 3:4 | ||||
| 46. Ronde | 04.05.2024 | Middlesbrough FC | - | Watford FC | 3:1 | |
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