| 4. Round | 20/08/2019 | Middlesbrough FC | - | Wigan Athletic | 1:0 | ||||
| 5. Round | 24/08/2019 | Middlesbrough FC | - | Millwall FC | 1:1 | ||||
| 6. Round | 31/08/2019 | Bristol City | - | Middlesbrough FC | 2:2 | ||||
| 7. Round | 14/09/2019 | Middlesbrough FC | - | Reading FC | 1:0 | ||||
| 9. Round | 28/09/2019 | Middlesbrough FC | - | Sheffield Wednesday | 1:4 | ||||
| 18. Round | 27/11/2019 | Middlesbrough FC | - | Barnsley FC | 1:0 |  |
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| 19. Round | 30/11/2019 | Leeds United | - | Middlesbrough FC | 4:0 |
England
Congo DR