| 1. Round | 05/08/2022 | Aston Villa U21 | - | Middlesbrough FC U21 | 3:3 |  |
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| 2. Round | 12/08/2022 | Middlesbrough FC U21 | - | Derby County U21 | 3:1 | ||||
| 3. Round | 22/08/2022 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 1:4 | ||||
| 6. Round | 18/09/2022 | Middlesbrough FC U21 | - | Norwich City U21 | 1:3 |  |
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| 7. Round | 30/09/2022 | Middlesbrough FC U21 | - | Newcastle United U21 | 1:1 | ||||
| 8. Round | 10/10/2022 | West Bromwich Albion U21 | - | Middlesbrough FC U21 | 5:2 | ||||
| 9. Round | 22/10/2022 | Middlesbrough FC U21 | - | Leeds United U21 | 2:4 | |
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| 12. Round | 09/01/2023 | Sunderland AFC U21 | - | Middlesbrough FC U21 | 5:7 | ||||
| 14. Round | 27/01/2023 | Middlesbrough FC U21 | - | Southampton FC U21 | 2:2 | ||||
| 15. Round | 10/02/2023 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 2:4 | |
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| 16. Round | 20/02/2023 | Stoke City U21 | - | Middlesbrough FC U21 | 1:2 | ||||
| 17. Round | 24/02/2023 | Norwich City U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 18. Round | 06/03/2023 | Middlesbrough FC U21 | - | Aston Villa U21 | 2:3 | ||||
| 13. Round | 24/03/2023 | Derby County U21 | - | Middlesbrough FC U21 | 1:5 | ||||
| 20. Round | 03/04/2023 | Newcastle United U21 | - | Middlesbrough FC U21 | 0:0 | |
England