| 1. Round | 09/08/2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 | ||||
| 2. Round | 16/08/2019 | Middlesbrough FC U23 | - | Stoke City U23 | 0:2 | ||||
| 3. Round | 23/08/2019 | Middlesbrough FC U23 | - | Swansea City U23 | 3:2 | ||||
| 4. Round | 30/08/2019 | Norwich City U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 5. Round | 16/09/2019 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 6. Round | 20/09/2019 | Middlesbrough FC U23 | - | West Ham United U23 | 3:4 | ||||
| 7. Round | 27/09/2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:4 | ||||
| 8. Round | 18/10/2019 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 |  |
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| 9. Round | 28/10/2019 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 10. Round | 04/11/2019 | Middlesbrough FC U23 | - | Manchester United U23 | 1:4 |  |
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| 11. Round | 25/11/2019 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 4:1 | ||||
| 13. Round | 16/12/2019 | Stoke City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 15. Round | 13/01/2020 | Swansea City U23 | - | Middlesbrough FC U23 | 5:1 | ||||
| 16. Round | 02/02/2020 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:0 | |
England