3. Ronde | 23.08.2019 | Middlesbrough FC U23 | - | Swansea City U23 | 3:2 | ||||
5. Ronde | 16.09.2019 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 2:3 | ||||
8. Ronde | 18.10.2019 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 | ||||
9. Ronde | 28.10.2019 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | ||||
10. Ronde | 04.11.2019 | Middlesbrough FC U23 | - | Manchester United U23 | 1:4 | ||||
13. Ronde | 16.12.2019 | Stoke City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
15. Ronde | 13.01.2020 | Swansea City U23 | - | Middlesbrough FC U23 | 5:1 |