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 | ||||
5. Round | 19/10/2020 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 0:6 | ||||
18. Round | 15/02/2021 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 1:1 | ||||
19. Round | 22/02/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 3:2 | ||||
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 | ||||
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 |