| 1. Round | 11/09/2020 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 2. Round | 21/09/2020 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 7. Round | 30/10/2020 | Norwich City U23 | - | Middlesbrough FC U23 | 1:3 | ||||
| 9. Round | 20/11/2020 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 1:4 | ||||
| 11. Round | 11/12/2020 | Fulham FC U23 | - | Middlesbrough FC U23 | 3:1 | ||||
| 19. Round | 22/02/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 3:2 | ||||
| 14. Round | 05/03/2021 | Middlesbrough FC U23 | - | Newcastle United U23 | 2:1 |  |
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| 24. Round | 16/04/2021 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:0 | ||||
| 25. Round | 23/04/2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 4:1 | ||||
| 13. Round | 07/05/2021 | Middlesbrough FC U23 | - | Crystal Palace U23 | 0:1 |
England