| 1. Ronde | 15.08.2016 | Middlesbrough FC U23 | - | Brighton & Hove Albion U23 | 0:0 | ||||
| 2. Ronde | 22.08.2016 | Blackburn Rovers U23 | - | Middlesbrough FC U23 | 0:0 | ||||
| 5. Ronde | 19.09.2016 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 2:1 | ||||
| 7. Ronde | 14.10.2016 | Stoke City U23 | - | Middlesbrough FC U23 | 3:1 | ||||
| 8. Ronde | 21.10.2016 | Middlesbrough FC U23 | - | West Ham United U23 | 0:1 | ||||
| 10. Ronde | 18.11.2016 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:4 | ||||
| 13. Ronde | 19.12.2016 | Swansea City U23 | - | Middlesbrough FC U23 | 3:2 |
Noord-Ierland