| 3. Ronde | 27.08.2018 | Stoke City U23 | - | Middlesbrough FC U23 | 1:1 | ||||
| 6. Ronde | 23.09.2018 | Middlesbrough FC U23 | - | Manchester United U23 | 0:2 | ||||
| 13. Ronde | 14.12.2018 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 2:2 | ||||
| 16. Ronde | 19.04.2019 | Middlesbrough FC U23 | - | Stoke City U23 | 2:2 | ||||
| 22. Ronde | 28.04.2019 | Middlesbrough FC U23 | - | Newcastle United U23 | 0:1 |
Engeland