| 1. Round | 04/08/2018 | Millwall FC | - | Middlesbrough FC | 2:2 |  |
|||
| 4. Round | 07/08/2018 | Middlesbrough FC | - | Sheffield United | 3:0 | |
|||
| 2. Round | 11/08/2018 | Middlesbrough FC | - | Birmingham City | 1:0 | ||||
| 3. Round | 18/08/2018 | Bristol City | - | Middlesbrough FC | 0:2 | |
|||
| 5. Round | 24/08/2018 | Middlesbrough FC | - | West Bromwich Albion | 1:0 | ||||
| 7. Round | 15/09/2018 | Norwich City | - | Middlesbrough FC | 1:0 | ||||
| 8. Round | 19/09/2018 | Middlesbrough FC | - | Bolton Wanderers | 2:0 | ||||
| 9. Round | 22/09/2018 | Middlesbrough FC | - | Swansea City | 0:0 | ||||
| 10. Round | 29/09/2018 | Hull City | - | Middlesbrough FC | 1:1 | ||||
| 11. Round | 02/10/2018 | Ipswich Town | - | Middlesbrough FC | 0:2 | ||||
| 12. Round | 06/10/2018 | Middlesbrough FC | - | Nottingham Forest | 0:2 | ||||
| 14. Round | 23/10/2018 | Middlesbrough FC | - | Rotherham United | 0:0 | ||||
| 15. Round | 27/10/2018 | Middlesbrough FC | - | Derby County | 1:1 | ||||
| 16. Round | 03/11/2018 | Stoke City | - | Middlesbrough FC | 0:0 | ||||
| 17. Round | 10/11/2018 | Middlesbrough FC | - | Wigan Athletic | 2:0 | ||||
| 19. Round | 27/11/2018 | Preston North End | - | Middlesbrough FC | 1:1 | ||||
| 20. Round | 01/12/2018 | Middlesbrough FC | - | Aston Villa | 0:3 |
Denmark
Guyana 
