| 16. Round | 02/11/2021 | Luton Town | - | Middlesbrough FC | 3:1 | ||||
| 17. Round | 06/11/2021 | West Bromwich Albion | - | Middlesbrough FC | 1:1 | ||||
| 18. Round | 20/11/2021 | Middlesbrough FC | - | Millwall FC | 1:1 | ||||
| 19. Round | 23/11/2021 | Middlesbrough FC | - | Preston North End | 1:2 | ||||
| 20. Round | 27/11/2021 | Huddersfield Town | - | Middlesbrough FC | 1:2 | ||||
| 21. Round | 04/12/2021 | Middlesbrough FC | - | Swansea City | 1:0 | ||||
| 42. Round | 15/04/2022 | AFC Bournemouth | - | Middlesbrough FC | 0:0 | ||||
| 43. Round | 18/04/2022 | Middlesbrough FC | - | Huddersfield Town | 0:2 | ||||
| 44. Round | 23/04/2022 | Swansea City | - | Middlesbrough FC | 1:1 | ||||
| 39. Round | 27/04/2022 | Middlesbrough FC | - | Cardiff City | 2:0 | ||||
| 45. Round | 30/04/2022 | Middlesbrough FC | - | Stoke City | 3:1 | ||||
| 46. Round | 07/05/2022 | Preston North End | - | Middlesbrough FC | 4:1 |  |
England
