| 1. Round | 16/08/2021 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 2:1 |  |
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| 2. Round | 20/08/2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | ||||
| 3. Round | 29/08/2021 | Middlesbrough FC U23 | - | Southampton FC U23 | 2:1 | ||||
| 4. Round | 13/09/2021 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 5. Round | 20/09/2021 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:3 | ||||
| 8. Round | 17/10/2021 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 1:2 |  |
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| 10. Round | 01/11/2021 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:0 | |
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| 11. Round | 07/11/2021 | Middlesbrough FC U23 | - | Birmingham City U23 | 0:3 | ||||
| 12. Round | 21/11/2021 | Middlesbrough FC U23 | - | Norwich City U23 | 3:2 | ||||
| 13. Round | 29/11/2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:1 | |
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| 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 | ||||
| 21. Round | 27/02/2022 | Birmingham City U23 | - | Middlesbrough FC U23 | 4:2 |
England