| 12. Round | 21/11/2021 | Middlesbrough FC U23 | - | Norwich City U23 | 3:2 |  |
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| 16. Round | 10/01/2022 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:2 | ||||
| 18. Round | 23/01/2022 | Southampton FC U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 22. Round | 14/03/2022 | Stoke City U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 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 |
England