| 1. Round | 11/08/2017 | Fulham FC U23 | - | Middlesbrough FC U23 | 1:2 |  |
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| 2. Round | 18/08/2017 | Middlesbrough FC U23 | - | Norwich City U23 | 4:0 | |
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| 3. Round | 25/08/2017 | Middlesbrough FC U23 | - | Newcastle United U23 | 1:0 | ||||
| 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 | ||||
| 7. Round | 15/10/2017 | Middlesbrough FC U23 | - | Reading FC U23 | 3:4 | |
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| 12. Round | 10/12/2017 | Norwich City U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 15. Round | 14/01/2018 | Middlesbrough FC U23 | - | Blackburn Rovers U23 | 3:3 |
England