| 13. Jornada | 19.10.2018 | Sheffield Wednesday | - | Middlesbrough | 1:2 | ||||
| 16. Jornada | 03.11.2018 | Stoke City | - | Middlesbrough | 0:0 | ||||
| 17. Jornada | 10.11.2018 | Middlesbrough | - | Wigan Athletic | 2:0 | ||||
| 18. Jornada | 24.11.2018 | Brentford FC | - | Middlesbrough | 1:2 | ||||
| 19. Jornada | 27.11.2018 | Preston North End | - | Middlesbrough | 1:1 | ||||
| 20. Jornada | 01.12.2018 | Middlesbrough | - | Aston Villa | 0:3 | ||||
| 25. Jornada | 29.12.2018 | Middlesbrough | - | Ipswich Town | 2:0 | ||||
| 26. Jornada | 01.01.2019 | Derby County | - | Middlesbrough | 1:1 | ||||
| 27. Jornada | 12.01.2019 | Birmingham City | - | Middlesbrough | 1:2 | ||||
| 28. Jornada | 19.01.2019 | Middlesbrough | - | Millwall FC | 1:1 |  |
Inglaterra
India