| 14. Round | 28/10/2023 | Middlesbrough FC | - | Stoke City | 0:2 | ||||
| 18. Round | 28/11/2023 | Middlesbrough FC | - | Preston North End | 4:0 | ||||
| 19. Round | 02/12/2023 | Leeds United | - | Middlesbrough FC | 3:2 | ||||
| 26. Round | 01/01/2024 | Middlesbrough FC | - | Coventry City | 1:3 | ||||
| 34. Round | 24/02/2024 | Middlesbrough FC | - | Plymouth Argyle | 0:2 | ||||
| 36. Round | 06/03/2024 | Middlesbrough FC | - | Norwich City | 3:1 | ||||
| 39. Round | 29/03/2024 | Southampton FC | - | Middlesbrough FC | 1:1 | ||||
| 40. Round | 01/04/2024 | Middlesbrough FC | - | Sheffield Wednesday | 2:0 | ||||
| 41. Round | 06/04/2024 | Middlesbrough FC | - | Swansea City | 2:0 | ||||
| 44. Round | 22/04/2024 | Middlesbrough FC | - | Leeds United | 3:4 | ||||
| 45. Round | 27/04/2024 | Cardiff City | - | Middlesbrough FC | 1:4 |  |
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| 46. Round | 04/05/2024 | Middlesbrough FC | - | Watford FC | 3:1 |
England