| 4. Round | 11/09/2017 | Blackburn Rovers U23 | - | Middlesbrough FC U23 | 1:3 | ||||
| 5. Round | 15/09/2017 | Middlesbrough FC U23 | - | Aston Villa U23 | 4:1 | ||||
| 6. Round | 22/09/2017 | Middlesbrough FC U23 | - | Stoke City U23 | 2:1 | ||||
| 7. Round | 15/10/2017 | Middlesbrough FC U23 | - | Reading FC U23 | 3:4 | ||||
| 9. Round | 29/10/2017 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 3:1 | ||||
| 10. Round | 20/11/2017 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 0:1 | ||||
| 11. Round | 26/11/2017 | Middlesbrough FC U23 | - | Southampton FC U23 | 3:3 |  |
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| 13. Round | 24/01/2018 | Middlesbrough FC U23 | - | Fulham FC U23 | 0:2 | ||||
| 16. Round | 29/01/2018 | Aston Villa U23 | - | Middlesbrough FC U23 | 4:0 | ||||
| 18. Round | 18/02/2018 | Reading FC U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 20. Round | 09/03/2018 | Middlesbrough FC U23 | - | Brighton & Hove Albion U23 | 0:3 | ||||
| 19. Round | 12/04/2018 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 1:1 | ||||
| 21. Round | 15/04/2018 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 2:1 |  |
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| 22. Round | 23/04/2018 | Southampton FC U23 | - | Middlesbrough FC U23 | 2:1 |
England