| 14. Round | 16/10/1998 | Portsmouth FC | - | Wolverhampton Wanderers | 1:0 | ||||
| 19. Round | 13/11/1998 | Norwich City | - | Wolverhampton Wanderers | 0:0 | ||||
| 24. Round | 18/12/1998 | Bradford City | - | Wolverhampton Wanderers | 2:1 | ||||
| 25. Round | 25/12/1998 | Swindon Town | - | Wolverhampton Wanderers | 1:0 | ||||
| 26. Round | 27/12/1998 | Wolverhampton Wanderers | - | Ipswich Town | 1:0 | ||||
| 27. Round | 07/01/1999 | Tranmere Rovers | - | Wolverhampton Wanderers | 1:2 | ||||
| 28. Round | 15/01/1999 | Wolverhampton Wanderers | - | Watford FC | 0:0 | ||||
| 29. Round | 29/01/1999 | Stockport County | - | Wolverhampton Wanderers | 1:2 | ||||
| 30. Round | 05/02/1999 | Wolverhampton Wanderers | - | Oxford United | 1:1 | ||||
| 31. Round | 12/02/1999 | Wolverhampton Wanderers | - | Port Vale FC | 3:1 | ||||
| 32. Round | 19/02/1999 | Sunderland AFC | - | Wolverhampton Wanderers | 2:1 | ||||
| 33. Round | 26/02/1999 | Wolverhampton Wanderers | - | Huddersfield Town | 2:2 | ||||
| 35. Round | 05/03/1999 | Queens Park Rangers | - | Wolverhampton Wanderers | 0:1 |  |
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| 37. Round | 12/03/1999 | Wolverhampton Wanderers | - | Bristol City | 3:0 | ||||
| 34. Round | 15/03/1999 | Bury FC | - | Wolverhampton Wanderers | 0:0 |
England