| 3. Round | 29/08/2021 | Middlesbrough FC U23 | - | Southampton FC U23 | 2:1 | ||||
| 9. Round | 22/10/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 11. Round | 07/11/2021 | Middlesbrough FC U23 | - | Birmingham City U23 | 0:3 | ||||
| 14. Round | 06/12/2021 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 3:2 | ||||
| 21. Round | 27/02/2022 | Birmingham City U23 | - | Middlesbrough FC U23 | 4:2 |  |
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| 22. Round | 14/03/2022 | Stoke City U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 23. Round | 18/03/2022 | Middlesbrough FC U23 | - | Fulham FC U23 | 0:0 | ||||
| 24. Round | 01/04/2022 | Middlesbrough FC U23 | - | Newcastle United U23 | 4:2 | ||||
| 20. Round | 15/04/2022 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 0:3 | ||||
| 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