| 2. Jornada | 10.08.2019 | Middlesbrough | - | Brentford FC | 0:1 | ||||
| 3. Jornada | 17.08.2019 | Blackburn Rovers | - | Middlesbrough | 1:0 |  |
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| 6. Jornada | 31.08.2019 | Bristol City | - | Middlesbrough | 2:2 | ||||
| 7. Jornada | 14.09.2019 | Middlesbrough | - | Reading | 1:0 | ||||
| 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 | |
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| 15. Jornada | 02.11.2019 | Derby County | - | Middlesbrough | 2:0 | ||||
| 16. Jornada | 09.11.2019 | Queens Park Rangers | - | Middlesbrough | 2:2 | ||||
| 17. Jornada | 24.11.2019 | Middlesbrough | - | Hull City | 2:2 | |
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| 18. Jornada | 27.11.2019 | Middlesbrough | - | Barnsley FC | 1:0 | ||||
| 42. Jornada | 08.07.2020 | Millwall FC | - | Middlesbrough | 0:2 | ||||
| 44. Jornada | 14.07.2020 | Reading | - | Middlesbrough | 1:2 | ||||
| 45. Jornada | 18.07.2020 | Middlesbrough | - | Cardiff City | 1:3 | ||||
| 46. Jornada | 22.07.2020 | Sheffield Wednesday | - | Middlesbrough | 1:2 |
Países Bajos