| 30. Round | 05/02/1999 | Wolverhampton Wanderers | - | Oxford United | 1:1 | ||||
| 31. Round | 12/02/1999 | Wolverhampton Wanderers | - | Port Vale FC | 3:1 |  |
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| 32. Round | 19/02/1999 | Sunderland AFC | - | Wolverhampton Wanderers | 2:1 | ||||
| 35. Round | 05/03/1999 | Queens Park Rangers | - | Wolverhampton Wanderers | 0:1 | ||||
| 37. Round | 12/03/1999 | Wolverhampton Wanderers | - | Bristol City | 3:0 | ||||
| 34. Round | 15/03/1999 | Bury FC | - | Wolverhampton Wanderers | 0:0 | ||||
| 36. Round | 29/03/1999 | Wolverhampton Wanderers | - | Crewe Alexandra | 3:0 | ||||
| 43. Round | 16/04/1999 | Birmingham City | - | Wolverhampton Wanderers | 0:1 | ||||
| 44. Round | 24/04/1999 | Wolverhampton Wanderers | - | West Bromwich Albion | 1:1 | ||||
| 39. Round | 03/05/1999 | Grimsby Town | - | Wolverhampton Wanderers | 0:0 | ||||
| 46. Round | 08/05/1999 | Wolverhampton Wanderers | - | Bradford City | 2:3 | |
England