3. Round | 27/08/2018 | Stoke City U23 | - | Middlesbrough FC U23 | 1:1 | ||||
6. Round | 23/09/2018 | Middlesbrough FC U23 | - | Manchester United U23 | 0:2 | ||||
13. Round | 14/12/2018 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 2:2 | ||||
16. Round | 19/04/2019 | Middlesbrough FC U23 | - | Stoke City U23 | 2:2 | ||||
22. Round | 28/04/2019 | Middlesbrough FC U23 | - | Newcastle United U23 | 0:1 |