| 13. Round | 16/12/2019 | Stoke City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 14. Round | 06/01/2020 | Middlesbrough FC U23 | - | Norwich City U23 | 3:4 | ||||
| 15. Round | 13/01/2020 | Swansea City U23 | - | Middlesbrough FC U23 | 5:1 | ||||
| 16. Round | 02/02/2020 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:0 | ||||
| 17. Round | 17/02/2020 | Reading FC U23 | - | Middlesbrough FC U23 | 0:1 | ||||
| 18. Round | 28/02/2020 | Middlesbrough FC U23 | - | Newcastle United U23 | 0:2 |
England