| 2. Round | 12/08/2022 | Middlesbrough FC U21 | - | Derby County U21 | 3:1 |  |
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| 3. Round | 22/08/2022 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 1:4 | ||||
| 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 |  |
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| 9. Round | 22/10/2022 | Middlesbrough FC U21 | - | Leeds United U21 | 2:4 | |
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| 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 |
England