1. Round | 10/08/2018 | Southampton FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
2. Round | 17/08/2018 | Middlesbrough FC U23 | - | Fulham FC U23 | 4:3 | ||||
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 | ||||
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 | ||||
20. Round | 07/04/2019 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 0:0 | ||||
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 |