| 1. Ronde | 10.08.2018 | Southampton FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 14. Ronde | 04.01.2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:2 |  |
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| 17. Ronde | 18.02.2019 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:1 | ||||
| 18. Ronde | 01.03.2019 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 0:0 | ||||
| 19. Ronde | 09.03.2019 | Reading FC U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 20. Ronde | 07.04.2019 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 0:0 | ||||
| 21. Ronde | 12.04.2019 | Norwich City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 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 |
Kosovo