12. Round | 07/12/2018 | Manchester United U23 | - | Middlesbrough FC U23 | 2:0 | ||||
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 | ||||
15. Round | 13/01/2019 | Middlesbrough FC U23 | - | Southampton FC U23 | 1:2 | ||||
17. Round | 18/02/2019 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:1 | ||||
18. Round | 01/03/2019 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 0:0 | ||||
19. Round | 09/03/2019 | Reading FC U23 | - | Middlesbrough FC 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 |