| 1. Jornada | 02.08.2019 | Luton Town | - | Middlesbrough | 3:3 | ||||
| 2. Jornada | 10.08.2019 | Middlesbrough | - | Brentford FC | 0:1 | ||||
| 3. Jornada | 17.08.2019 | Blackburn Rovers | - | Middlesbrough | 1:0 | ||||
| 4. Jornada | 20.08.2019 | Middlesbrough | - | Wigan Athletic | 1:0 |  |
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| 5. Jornada | 24.08.2019 | Middlesbrough | - | Millwall FC | 1:1 | ||||
| 8. Jornada | 21.09.2019 | Cardiff City | - | Middlesbrough | 1:0 | ||||
| 9. Jornada | 28.09.2019 | Middlesbrough | - | Sheffield Wednesday | 1:4 | ||||
| 10. Jornada | 01.10.2019 | Middlesbrough | - | Preston North End | 1:1 | ||||
| 11. Jornada | 04.10.2019 | Birmingham City | - | Middlesbrough | 2:1 | ||||
| 12. Jornada | 19.10.2019 | Middlesbrough | - | West Bromwich Albion | 0:1 | ||||
| 14. Jornada | 26.10.2019 | Middlesbrough | - | Fulham FC | 0:0 | ||||
| 15. Jornada | 02.11.2019 | Derby County | - | Middlesbrough | 2:0 | ||||
| 22. Jornada | 14.12.2019 | Swansea City | - | Middlesbrough | 3:1 | |
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Inglaterra