| 4. Ronde | 20.08.2019 | Middlesbrough FC | - | Wigan Athletic | 1:0 | ||||
| 5. Ronde | 24.08.2019 | Middlesbrough FC | - | Millwall FC | 1:1 | ||||
| 6. Ronde | 31.08.2019 | Bristol City | - | Middlesbrough FC | 2:2 | ||||
| 7. Ronde | 14.09.2019 | Middlesbrough FC | - | Reading FC | 1:0 | ||||
| 9. Ronde | 28.09.2019 | Middlesbrough FC | - | Sheffield Wednesday | 1:4 | ||||
| 18. Ronde | 27.11.2019 | Middlesbrough FC | - | Barnsley FC | 1:0 |  |
|||
| 19. Ronde | 30.11.2019 | Leeds United | - | Middlesbrough FC | 4:0 |
Engeland
Congo DR