| 3. Round | 23/08/2019 | Middlesbrough FC U23 | - | Swansea City U23 | 3:2 | ||||
| 5. Round | 16/09/2019 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 2:3 |  |
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| 8. Round | 18/10/2019 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 | ||||
| 9. Round | 28/10/2019 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | |
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| 10. Round | 04/11/2019 | Middlesbrough FC U23 | - | Manchester United U23 | 1:4 | ||||
| 13. Round | 16/12/2019 | Stoke City U23 | - | Middlesbrough FC U23 | 2:3 |  |
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| 15. Round | 13/01/2020 | Swansea City U23 | - | Middlesbrough FC U23 | 5:1 | |
England