| 27. Round | 11/01/2020 | Middlesbrough FC | - | Derby County | 2:2 | ||||
| 28. Round | 17/01/2020 | Fulham FC | - | Middlesbrough FC | 1:0 | ||||
| 29. Round | 21/01/2020 | Middlesbrough FC | - | Birmingham City | 1:1 | ||||
| 38. Round | 20/06/2020 | Middlesbrough FC | - | Swansea City | 0:3 |  |
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| 39. Round | 27/06/2020 | Stoke City | - | Middlesbrough FC | 0:2 | ||||
| 40. Round | 02/07/2020 | Hull City | - | Middlesbrough FC | 2:1 | ||||
| 41. Round | 05/07/2020 | Middlesbrough FC | - | Queens Park Rangers | 0:1 | ||||
| 43. Round | 11/07/2020 | Middlesbrough FC | - | Bristol City | 1:3 | ||||
| 44. Round | 14/07/2020 | Reading FC | - | Middlesbrough FC | 1:2 |  |
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| 45. Round | 18/07/2020 | Middlesbrough FC | - | Cardiff City | 1:3 |
England
