| 7. Round | 07/09/1998 | Sheffield United | - | Grimsby Town | 3:2 | ||||
| 8. Round | 11/09/1998 | Bradford City | - | Sheffield United | 2:2 | ||||
| 9. Round | 18/09/1998 | Sheffield United | - | Norwich City | 2:1 | ||||
| 10. Round | 26/09/1998 | Crystal Palace | - | Sheffield United | 1:0 | ||||
| 15. Round | 19/10/1998 | Sheffield United | - | Stockport County | 1:1 | ||||
| 16. Round | 23/10/1998 | Oxford United | - | Sheffield United | 0:2 | ||||
| 17. Round | 30/10/1998 | Port Vale FC | - | Sheffield United | 2:3 |
Scotland
