| 2. Ronde | 20.08.2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | ||||
| 3. Ronde | 29.08.2021 | Middlesbrough FC U23 | - | Southampton FC U23 | 2:1 |  |
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| 6. Ronde | 24.09.2021 | Middlesbrough FC U23 | - | Nottingham Forest U23 | 0:1 | ||||
| 8. Ronde | 17.10.2021 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 1:2 | ||||
| 10. Ronde | 01.11.2021 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 13. Ronde | 29.11.2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:1 | ||||
| 14. Ronde | 06.12.2021 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 3:2 | ||||
| 22. Ronde | 14.03.2022 | Stoke City U23 | - | Middlesbrough FC U23 | 1:0 |
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