| 1. Round | 11/08/2018 | Reading FC U23 | - | Wolverhampton Wanderers U23 | 2:2 |  |
|||
| 2. Round | 17/08/2018 | Wolverhampton Wanderers U23 | - | West Bromwich Albion U23 | 4:1 | |
|||
| 4. Round | 31/08/2018 | Norwich City U23 | - | Wolverhampton Wanderers U23 | 1:3 | |
|||
| 8. Round | 19/10/2018 | Southampton FC U23 | - | Wolverhampton Wanderers U23 | 3:2 | ||||
| 9. Round | 26/10/2018 | Wolverhampton Wanderers U23 | - | Manchester United U23 | 2:1 | |
|||
| 10. Round | 02/11/2018 | Stoke City U23 | - | Wolverhampton Wanderers U23 | 2:2 | |
|||
| 11. Round | 26/11/2018 | Wolverhampton Wanderers U23 | - | Aston Villa U23 | 0:0 | ||||
| 12. Round | 09/12/2018 | Sunderland AFC U23 | - | Wolverhampton Wanderers U23 | 0:1 | ||||
| 14. Round | 07/01/2019 | West Bromwich Albion U23 | - | Wolverhampton Wanderers U23 | 2:4 | ||||
| 15. Round | 11/01/2019 | Wolverhampton Wanderers U23 | - | Reading FC U23 | 1:2 |
England