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 | ||||
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 | ||||
15. Round | 25/01/2021 | Stoke City U23 | - | Middlesbrough FC U23 | 2:0 |