| 1. Ronde | 09.08.2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 | ||||
| 5. Ronde | 16.09.2019 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 2:3 |  |
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| 8. Ronde | 18.10.2019 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 | ||||
| 10. Ronde | 04.11.2019 | Middlesbrough FC U23 | - | Manchester United U23 | 1:4 | ||||
| 11. Ronde | 25.11.2019 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 4:1 |
Engeland
Jamaica