3. Round | 27/08/2018 | Stoke City U23 | - | Middlesbrough FC U23 | 1:1 | ||||
5. Round | 17/09/2018 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 2:3 | ||||
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 | ||||
14. Round | 04/01/2019 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:2 | ||||
21. Round | 12/04/2019 | Norwich City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
16. Round | 19/04/2019 | Middlesbrough FC U23 | - | Stoke City U23 | 2:2 |