| 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 | |
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| 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 | |
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| 6. Round | 24/09/2021 | Middlesbrough FC U23 | - | Nottingham Forest U23 | 0:1 | ||||
| 7. Round | 01/10/2021 | Newcastle United U23 | - | Middlesbrough FC U23 | 4:1 | |
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| 13. Round | 29/11/2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:1 | ||||
| 16. Round | 10/01/2022 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:2 | ||||
| 17. Round | 16/01/2022 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 3:2 | ||||
| 18. Round | 23/01/2022 | Southampton FC U23 | - | Middlesbrough FC U23 | 1:0 |
England