2. Round | 16/08/2019 | Middlesbrough FC U23 | - | Stoke City U23 | 0:2 | ||||
6. Round | 20/09/2019 | Middlesbrough FC U23 | - | West Ham United U23 | 3:4 | ||||
7. Round | 27/09/2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:4 | ||||
8. Round | 18/10/2019 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 | ||||
11. Round | 25/11/2019 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 4:1 | ||||
12. Round | 09/12/2019 | Aston Villa U23 | - | Middlesbrough FC U23 | 5:3 | ||||
15. Round | 13/01/2020 | Swansea City U23 | - | Middlesbrough FC U23 | 5:1 | ||||
16. Round | 02/02/2020 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:0 | ||||
17. Round | 17/02/2020 | Reading FC U23 | - | Middlesbrough FC U23 | 0:1 | ||||
18. Round | 28/02/2020 | Middlesbrough FC U23 | - | Newcastle United U23 | 0:2 |