| 2. Round | 21/09/2020 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 15. Round | 25/01/2021 | Stoke City U23 | - | Middlesbrough FC U23 | 2:0 |  |
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| 20. Round | 26/02/2021 | Middlesbrough FC U23 | - | Norwich City U23 | 0:3 | ||||
| 14. Round | 05/03/2021 | Middlesbrough FC U23 | - | Newcastle United U23 | 2:1 | ||||
| 21. Round | 12/03/2021 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 0:1 | ||||
| 22. Round | 22/03/2021 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 1:1 | ||||
| 23. Round | 09/04/2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:4 | ||||
| 26. Round | 03/05/2021 | Crystal Palace U23 | - | Middlesbrough FC U23 | 3:2 |  |
England