1. Round | 09/08/2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 | ||||
2. Round | 16/08/2019 | Middlesbrough FC U23 | - | Stoke City U23 | 0:2 | ||||
3. Round | 23/08/2019 | Middlesbrough FC U23 | - | Swansea City U23 | 3:2 | ||||
4. Round | 30/08/2019 | Norwich City U23 | - | Middlesbrough FC U23 | 2:2 | ||||
9. Round | 28/10/2019 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 |