| 1. Round | 09/08/2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 | ||||
| 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 | ||||
| 10. Round | 04/11/2019 | Middlesbrough FC U23 | - | Manchester United U23 | 1:4 | ||||
| 11. Round | 25/11/2019 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 4:1 |
England
Jamaica 