| 27. Round | 30/01/2021 | Norwich City | - | Middlesbrough FC | 0:0 | ||||
| 28. Round | 06/02/2021 | Middlesbrough FC | - | Brentford FC | 1:4 | ||||
| 34. Round | 02/03/2021 | Coventry City | - | Middlesbrough FC | 1:2 | ||||
| 35. Round | 06/03/2021 | Swansea City | - | Middlesbrough FC | 2:1 |  |
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| 36. Round | 13/03/2021 | Middlesbrough FC | - | Stoke City | 3:0 | ||||
| 37. Round | 16/03/2021 | Middlesbrough FC | - | Preston North End | 2:0 | ||||
| 38. Round | 20/03/2021 | Millwall FC | - | Middlesbrough FC | 1:0 | ||||
| 39. Round | 02/04/2021 | AFC Bournemouth | - | Middlesbrough FC | 3:1 | ||||
| 40. Round | 05/04/2021 | Middlesbrough FC | - | Watford FC | 1:1 |  |
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| 41. Round | 10/04/2021 | Barnsley FC | - | Middlesbrough FC | 2:0 | ||||
| 42. Round | 17/04/2021 | Middlesbrough FC | - | Queens Park Rangers | 1:2 | |
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| 43. Round | 21/04/2021 | Rotherham United | - | Middlesbrough FC | 1:2 | ||||
| 44. Round | 24/04/2021 | Middlesbrough FC | - | Sheffield Wednesday | 3:1 | |
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| 45. Round | 01/05/2021 | Luton Town | - | Middlesbrough FC | 1:1 | ||||
| 46. Round | 08/05/2021 | Middlesbrough FC | - | Wycombe Wanderers | 0:3 |
France
England 
