| 8. Round | 21/10/2016 | Middlesbrough FC U23 | - | West Ham United U23 | 0:1 |  |
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| 9. Round | 31/10/2016 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:0 | |
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| 11. Round | 28/11/2016 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 0:0 | ||||
| 21. Round | 10/04/2017 | West Ham United U23 | - | Middlesbrough FC U23 | 1:3 |  |
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| 14. Round | 17/04/2017 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 0:1 | ||||
| 22. Round | 21/04/2017 | Middlesbrough FC U23 | - | Newcastle United U23 | 0:2 | |
England