| 2. Round | 18/08/2017 | Middlesbrough FC U23 | - | Norwich City U23 | 4:0 | ||||
| 5. Round | 15/09/2017 | Middlesbrough FC U23 | - | Aston Villa U23 | 4:1 |  |
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| 7. Round | 15/10/2017 | Middlesbrough FC U23 | - | Reading FC U23 | 3:4 | ||||
| 12. Round | 10/12/2017 | Norwich City U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 16. Round | 29/01/2018 | Aston Villa U23 | - | Middlesbrough FC U23 | 4:0 | ||||
| 17. Round | 05/02/2018 | Stoke City U23 | - | Middlesbrough FC U23 | 3:2 | |
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| 20. Round | 09/03/2018 | Middlesbrough FC U23 | - | Brighton & Hove Albion U23 | 0:3 | ||||
| 14. Round | 03/04/2018 | Newcastle United U23 | - | Middlesbrough FC U23 | 0:1 | ||||
| 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 | ||||
| 22. Round | 23/04/2018 | Southampton FC U23 | - | Middlesbrough FC U23 | 2:1 |
England