1. Round | 11/09/2020 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | ||||
4. Round | 02/10/2020 | Leeds United U23 | - | Middlesbrough FC U23 | 1:0 | ||||
15. Round | 25/01/2021 | Stoke City U23 | - | Middlesbrough FC U23 | 2:0 | ||||
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 | ||||
24. Round | 16/04/2021 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:0 |