| 2. Ronde | 17.08.2018 | Middlesbrough FC U23 | - | Fulham FC U23 | 4:3 |  |
 |
||
| 3. Ronde | 27.08.2018 | Stoke City U23 | - | Middlesbrough FC U23 | 1:1 | ||||
| 4. Ronde | 02.09.2018 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | |
|||
| 5. Ronde | 17.09.2018 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 6. Ronde | 23.09.2018 | Middlesbrough FC U23 | - | Manchester United U23 | 0:2 | ||||
| 7. Ronde | 28.09.2018 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 8. Ronde | 19.10.2018 | Middlesbrough FC U23 | - | Reading FC U23 | 2:3 | ||||
| 9. Ronde | 26.10.2018 | Newcastle United U23 | - | Middlesbrough FC U23 | 1:3 | |
|||
| 10. Ronde | 04.11.2018 | Middlesbrough FC U23 | - | Norwich City U23 | 2:1 | ||||
| 11. Ronde | 26.11.2018 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:3 | |
|||
| 14. Ronde | 04.01.2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:2 | |
|||
| 15. Ronde | 13.01.2019 | Middlesbrough FC U23 | - | Southampton FC U23 | 1:2 | |
Engeland