3. Round | 17/08/2019 | Blackburn Rovers | - | Middlesbrough FC | 1:0 | ||||
9. Round | 28/09/2019 | Middlesbrough FC | - | Sheffield Wednesday | 1:4 | ||||
15. Round | 02/11/2019 | Derby County | - | Middlesbrough FC | 2:0 | ||||
19. Round | 30/11/2019 | Leeds United | - | Middlesbrough FC | 4:0 | ||||
20. Round | 07/12/2019 | Middlesbrough FC | - | Charlton Athletic | 1:0 | ||||
21. Round | 10/12/2019 | Nottingham Forest | - | Middlesbrough FC | 1:1 | ||||
23. Round | 20/12/2019 | Middlesbrough FC | - | Stoke City | 2:1 |