| 1. Round | 05/08/2017 | Wolverhampton Wanderers | - | Middlesbrough FC | 1:0 |  |
|||
| 2. Round | 12/08/2017 | Middlesbrough FC | - | Sheffield United | 1:0 | ||||
| 3. Round | 15/08/2017 | Middlesbrough FC | - | Burton Albion | 2:0 | ||||
| 4. Round | 19/08/2017 | Nottingham Forest | - | Middlesbrough FC | 2:1 | ||||
| 8. Round | 16/09/2017 | Middlesbrough FC | - | Queens Park Rangers | 3:2 | ||||
| 14. Round | 28/10/2017 | Reading FC | - | Middlesbrough FC | 0:2 | ||||
| 16. Round | 05/11/2017 | Middlesbrough FC | - | Sunderland AFC | 1:0 | ||||
| 18. Round | 22/11/2017 | Middlesbrough FC | - | Birmingham City | 2:0 | ||||
| 19. Round | 25/11/2017 | Middlesbrough FC | - | Derby County | 0:3 | ||||
| 20. Round | 02/12/2017 | Bristol City | - | Middlesbrough FC | 2:1 | ||||
| 21. Round | 09/12/2017 | Middlesbrough FC | - | Ipswich Town | 2:0 |
England