| 13. Ronde | 16.12.2019 | Stoke City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 14. Ronde | 06.01.2020 | Middlesbrough FC U23 | - | Norwich City U23 | 3:4 | ||||
| 15. Ronde | 13.01.2020 | Swansea City U23 | - | Middlesbrough FC U23 | 5:1 | ||||
| 16. Ronde | 02.02.2020 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:0 | ||||
| 17. Ronde | 17.02.2020 | Reading FC U23 | - | Middlesbrough FC U23 | 0:1 | ||||
| 18. Ronde | 28.02.2020 | Middlesbrough FC U23 | - | Newcastle United U23 | 0:2 |
Engeland