| 1. Round | 16/08/2021 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 2:1 |  |
|||
| 2. Round | 20/08/2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | ||||
| 4. Round | 13/09/2021 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 6. Round | 24/09/2021 | Middlesbrough FC U23 | - | Nottingham Forest U23 | 0:1 | ||||
| 7. Round | 01/10/2021 | Newcastle United U23 | - | Middlesbrough FC U23 | 4:1 | ||||
| 8. Round | 17/10/2021 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 1:2 | ||||
| 9. Round | 22/10/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 10. Round | 01/11/2021 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 13. Round | 29/11/2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:1 | ||||
| 14. Round | 06/12/2021 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 3:2 |
England