| 1. Ronde | 09.08.2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 |  |
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| 2. Ronde | 16.08.2019 | Middlesbrough FC U23 | - | Stoke City U23 | 0:2 | ||||
| 3. Ronde | 23.08.2019 | Middlesbrough FC U23 | - | Swansea City U23 | 3:2 | |
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| 4. Ronde | 30.08.2019 | Norwich City U23 | - | Middlesbrough FC U23 | 2:2 | |
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| 7. Ronde | 27.09.2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:4 | |
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| 9. Ronde | 28.10.2019 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | |
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| 10. Ronde | 04.11.2019 | Middlesbrough FC U23 | - | Manchester United U23 | 1:4 | ||||
| 13. Ronde | 16.12.2019 | Stoke City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 14. Ronde | 06.01.2020 | Middlesbrough FC U23 | - | Norwich City U23 | 3:4 | |
Engeland