| 13. Round | 19/10/2018 | Sheffield Wednesday | - | Middlesbrough FC | 1:2 | ||||
| 16. Round | 03/11/2018 | Stoke City | - | Middlesbrough FC | 0:0 | ||||
| 17. Round | 10/11/2018 | Middlesbrough FC | - | Wigan Athletic | 2:0 | ||||
| 18. Round | 24/11/2018 | Brentford FC | - | Middlesbrough FC | 1:2 | ||||
| 19. Round | 27/11/2018 | Preston North End | - | Middlesbrough FC | 1:1 | ||||
| 20. Round | 01/12/2018 | Middlesbrough FC | - | Aston Villa | 0:3 | ||||
| 25. Round | 29/12/2018 | Middlesbrough FC | - | Ipswich Town | 2:0 | ||||
| 26. Round | 01/01/2019 | Derby County | - | Middlesbrough FC | 1:1 | ||||
| 27. Round | 12/01/2019 | Birmingham City | - | Middlesbrough FC | 1:2 | ||||
| 28. Round | 19/01/2019 | Middlesbrough FC | - | Millwall FC | 1:1 |  |
England
India 
