| 3. Round | 29/08/2021 | Middlesbrough FC U23 | - | Southampton FC U23 | 2:1 |  |
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| 4. Round | 13/09/2021 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | |
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| 5. Round | 20/09/2021 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:3 | |
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| 17. Round | 16/01/2022 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 3:2 | ||||
| 21. Round | 27/02/2022 | Birmingham City U23 | - | Middlesbrough FC U23 | 4:2 |
England