| 1. Ronde | 09.08.2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 | ||||
| 2. Ronde | 16.08.2019 | Middlesbrough FC U23 | - | Stoke City U23 | 0:2 |  |
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| 3. Ronde | 23.08.2019 | Middlesbrough FC U23 | - | Swansea City U23 | 3:2 | ||||
| 4. Ronde | 30.08.2019 | Norwich City U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 5. Ronde | 16.09.2019 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 7. Ronde | 27.09.2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:4 | ||||
| 8. Ronde | 18.10.2019 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 | ||||
| 11. Ronde | 25.11.2019 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 4:1 | ||||
| 12. Ronde | 09.12.2019 | Aston Villa U23 | - | Middlesbrough FC U23 | 5:3 |  |
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| 13. Ronde | 16.12.2019 | Stoke City U23 | - | Middlesbrough FC U23 | 2:3 | |
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| 14. Ronde | 06.01.2020 | Middlesbrough FC U23 | - | Norwich City U23 | 3:4 | ||||
| 15. Ronde | 13.01.2020 | Swansea City U23 | - | Middlesbrough FC U23 | 5:1 |
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