| 3. Ronde | 17.08.2019 | Blackburn Rovers | - | Middlesbrough FC | 1:0 | ||||
| 9. Ronde | 28.09.2019 | Middlesbrough FC | - | Sheffield Wednesday | 1:4 | ||||
| 15. Ronde | 02.11.2019 | Derby County | - | Middlesbrough FC | 2:0 | ||||
| 19. Ronde | 30.11.2019 | Leeds United | - | Middlesbrough FC | 4:0 | ||||
| 20. Ronde | 07.12.2019 | Middlesbrough FC | - | Charlton Athletic | 1:0 | ||||
| 21. Ronde | 10.12.2019 | Nottingham Forest | - | Middlesbrough FC | 1:1 | ||||
| 23. Ronde | 20.12.2019 | Middlesbrough FC | - | Stoke City | 2:1 |
Engeland