| 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 | ||||
| 7. Round | 14/10/2016 | Stoke City U23 | - | Middlesbrough FC U23 | 3:1 | ||||
| 8. Round | 21/10/2016 | Middlesbrough FC U23 | - | West Ham United U23 | 0:1 | ||||
| 9. Round | 31/10/2016 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 11. Round | 28/11/2016 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 0:0 | ||||
| 12. Round | 12/12/2016 | Middlesbrough FC U23 | - | Norwich City U23 | 2:2 | ||||
| 13. Round | 19/12/2016 | Swansea City U23 | - | Middlesbrough FC U23 | 3:2 |
England