| 1. Round | 16/08/2021 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 2:1 | ||||
| 2. Round | 20/08/2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | ||||
| 17. Round | 16/01/2022 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 3:2 |  |
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| 21. Round | 27/02/2022 | Birmingham City U23 | - | Middlesbrough FC U23 | 4:2 | ||||
| 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 | ||||
| 26. Round | 01/05/2022 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 |
England
Jamaica