| 8. Round | 17/10/2021 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 1:2 |  |
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| 9. Round | 22/10/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 15. Round | 19/12/2021 | Middlesbrough FC U23 | - | Burnley FC U23 | 0:3 |  |
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| 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 |
Ireland