| 4. Ronde | 02.09.2018 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | ||||
| 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 |  |
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| 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 |
Engeland