| 1. Ronde | 16.08.2021 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 2:1 |  |
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| 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 | ||||
| 4. Ronde | 13.09.2021 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 5. Ronde | 20.09.2021 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:3 | ||||
| 8. Ronde | 17.10.2021 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 1:2 |  |
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| 10. Ronde | 01.11.2021 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:0 | |
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| 11. Ronde | 07.11.2021 | Middlesbrough FC U23 | - | Birmingham City U23 | 0:3 | ||||
| 12. Ronde | 21.11.2021 | Middlesbrough FC U23 | - | Norwich City U23 | 3:2 | ||||
| 13. Ronde | 29.11.2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:1 | |
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| 15. Ronde | 19.12.2021 | Middlesbrough FC U23 | - | Burnley FC U23 | 0:3 | ||||
| 16. Ronde | 10.01.2022 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:2 | |
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| 17. Ronde | 16.01.2022 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 3:2 | ||||
| 21. Ronde | 27.02.2022 | Birmingham City U23 | - | Middlesbrough FC U23 | 4:2 |
Engeland