| 1. Round | 15/08/2016 | Middlesbrough FC U23 | - | Brighton & Hove Albion U23 | 0:0 | ||||
| 2. Round | 22/08/2016 | Blackburn Rovers U23 | - | Middlesbrough FC U23 | 0:0 | ||||
| 3. Round | 25/08/2016 | Norwich City U23 | - | Middlesbrough FC U23 | 1:2 | ||||
| 4. Round | 12/09/2016 | Middlesbrough FC U23 | - | Swansea City U23 | 2:1 | ||||
| 6. Round | 26/09/2016 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | ||||
| 7. Round | 14/10/2016 | Stoke City U23 | - | Middlesbrough FC U23 | 3:1 |  |
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| 16. Round | 30/01/2017 | Middlesbrough FC U23 | - | Stoke City U23 | 2:2 | ||||
| 17. Round | 06/02/2017 | Fulham FC U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 18. Round | 20/02/2017 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 2:1 |  |
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| 19. Round | 03/03/2017 | Brighton & Hove Albion U23 | - | Middlesbrough FC U23 | 4:2 |  |
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| 20. Round | 13/03/2017 | Middlesbrough FC U23 | - | Blackburn Rovers U23 | 4:1 | |
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| 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