| 11. Round | 11/12/2020 | Fulham FC U23 | - | Middlesbrough FC U23 | 3:1 |  |
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| 12. Round | 18/12/2020 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:1 |  |
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| 19. Round | 22/02/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 3:2 | ||||
| 20. Round | 26/02/2021 | Middlesbrough FC U23 | - | Norwich City U23 | 0:3 | ||||
| 14. Round | 05/03/2021 | Middlesbrough FC U23 | - | Newcastle United U23 | 2:1 | ||||
| 21. Round | 12/03/2021 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 0:1 | ||||
| 25. Round | 23/04/2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 4:1 | ||||
| 13. Round | 07/05/2021 | Middlesbrough FC U23 | - | Crystal Palace U23 | 0:1 | |
Kenya
Germany