4. Round | 02/10/2020 | Leeds United U23 | - | Middlesbrough FC U23 | 1:0 | ||||
5. Round | 19/10/2020 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 0:6 | ||||
6. Round | 23/10/2020 | Middlesbrough FC U23 | - | Burnley FC U23 | 3:0 | ||||
7. Round | 30/10/2020 | Norwich City U23 | - | Middlesbrough FC U23 | 1:3 | ||||
8. Round | 08/11/2020 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 0:1 | ||||
9. Round | 20/11/2020 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 1:4 | ||||
10. Round | 27/11/2020 | Middlesbrough FC U23 | - | Reading FC U23 | 2:3 | ||||
11. Round | 11/12/2020 | Fulham FC U23 | - | Middlesbrough FC U23 | 3:1 | ||||
12. Round | 18/12/2020 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:1 | ||||
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 | ||||
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 | ||||
26. Round | 03/05/2021 | Crystal Palace U23 | - | Middlesbrough FC U23 | 3:2 | ||||
13. Round | 07/05/2021 | Middlesbrough FC U23 | - | Crystal Palace U23 | 0:1 |