| 6. Jornada | 11.09.2021 | Coventry City | - | Middlesbrough | 2:0 | ||||
| 7. Jornada | 15.09.2021 | Nottingham Forest | - | Middlesbrough | 0:2 |  |
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| 8. Jornada | 18.09.2021 | Middlesbrough | - | Blackpool FC | 1:2 | ||||
| 12. Jornada | 16.10.2021 | Middlesbrough | - | Peterborough United | 2:0 | ||||
| 13. Jornada | 20.10.2021 | Middlesbrough | - | Barnsley FC | 2:0 | ||||
| 14. Jornada | 23.10.2021 | Cardiff City | - | Middlesbrough | 0:2 | ||||
| 15. Jornada | 30.10.2021 | Middlesbrough | - | Birmingham City | 0:2 | ||||
| 16. Jornada | 02.11.2021 | Luton Town | - | Middlesbrough | 3:1 | ||||
| 17. Jornada | 06.11.2021 | West Bromwich Albion | - | Middlesbrough | 1:1 | ||||
| 18. Jornada | 20.11.2021 | Middlesbrough | - | Millwall FC | 1:1 | ||||
| 19. Jornada | 23.11.2021 | Middlesbrough | - | Preston North End | 1:2 | ||||
| 20. Jornada | 27.11.2021 | Huddersfield Town | - | Middlesbrough | 1:2 | ||||
| 21. Jornada | 04.12.2021 | Middlesbrough | - | Swansea City | 1:0 | ||||
| 22. Jornada | 11.12.2021 | Stoke City | - | Middlesbrough | 0:0 | ||||
| 23. Jornada | 18.12.2021 | Middlesbrough | - | Bournemouth | 1:0 | |
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| 24. Jornada | 26.12.2021 | Middlesbrough | - | Nottingham Forest | 2:0 | ||||
| 25. Jornada | 29.12.2021 | Blackpool FC | - | Middlesbrough | 1:2 |
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