| 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 | ||||
| 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 | ||||
| 5. Round | 23/09/2022 | Middlesbrough FC U21 | - | Sunderland AFC U21 | 2:0 |  |
|||
| 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 | ||||
| 10. Round | 30/10/2022 | Southampton FC U21 | - | Middlesbrough FC U21 | 8:1 | ||||
| 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 |
England