| 1. Ronde | 10.08.2018 | Southampton FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 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 | ||||
| 6. Ronde | 23.09.2018 | Middlesbrough FC U23 | - | Manchester United U23 | 0:2 |  |
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| 14. Ronde | 04.01.2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:2 | |
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| 15. Ronde | 13.01.2019 | Middlesbrough FC U23 | - | Southampton FC U23 | 1:2 | ||||
| 17. Ronde | 18.02.2019 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:1 | |
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| 18. Ronde | 01.03.2019 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 0:0 | ||||
| 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 |
Engeland