| 2. Ronde | 21.09.2020 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 15. Ronde | 25.01.2021 | Stoke City U23 | - | Middlesbrough FC U23 | 2:0 |  |
|||
| 20. Ronde | 26.02.2021 | Middlesbrough FC U23 | - | Norwich City U23 | 0:3 | ||||
| 14. Ronde | 05.03.2021 | Middlesbrough FC U23 | - | Newcastle United U23 | 2:1 | ||||
| 21. Ronde | 12.03.2021 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 0:1 | ||||
| 22. Ronde | 22.03.2021 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 1:1 | ||||
| 23. Ronde | 09.04.2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:4 | ||||
| 26. Ronde | 03.05.2021 | Crystal Palace U23 | - | Middlesbrough FC U23 | 3:2 |  |
Engeland