| 7. Round | 01/10/2021 | Newcastle United U23 | - | Middlesbrough FC U23 | 4:1 | ||||
| 8. Round | 17/10/2021 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 1:2 | ||||
| 9. Round | 22/10/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 2:0 |  |
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| 10. Round | 01/11/2021 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:0 |  |
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| 12. Round | 21/11/2021 | Middlesbrough FC U23 | - | Norwich City U23 | 3:2 | ||||
| 15. Round | 19/12/2021 | Middlesbrough FC U23 | - | Burnley FC U23 | 0:3 | ||||
| 16. Round | 10/01/2022 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:2 | |
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| 17. Round | 16/01/2022 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 3:2 | |
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| 18. Round | 23/01/2022 | Southampton FC U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 21. Round | 27/02/2022 | Birmingham City U23 | - | Middlesbrough FC U23 | 4:2 | ||||
| 22. Round | 14/03/2022 | Stoke City U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 23. Round | 18/03/2022 | Middlesbrough FC U23 | - | Fulham FC U23 | 0:0 | ||||
| 25. Round | 22/04/2022 | Nottingham Forest U23 | - | Middlesbrough FC U23 | 1:1 | ||||
| 26. Round | 01/05/2022 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 |
Kenya
Germany