| 1. Round | 05/08/2022 | Aston Villa U21 | - | Middlesbrough FC U21 | 3:3 | ||||
| 3. Round | 22/08/2022 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 1:4 |  |
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| 4. Round | 26/08/2022 | Middlesbrough FC U21 | - | Stoke City U21 | 4:1 | ||||
| 6. Round | 18/09/2022 | Middlesbrough FC U21 | - | Norwich City U21 | 1:3 | |
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| 5. Round | 23/09/2022 | Middlesbrough FC U21 | - | Sunderland AFC U21 | 2:0 |  |
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| 7. Round | 30/09/2022 | Middlesbrough FC U21 | - | Newcastle United U21 | 1:1 | |
England