1. Round | 07/08/1998 | Wolverhampton Wanderers | - | Tranmere Rovers | 2:0 | ||||
2. Round | 14/08/1998 | Oxford United | - | Wolverhampton Wanderers | 0:2 | ||||
3. Round | 21/08/1998 | Wolverhampton Wanderers | - | Swindon Town | 1:0 | ||||
4. Round | 27/08/1998 | Watford FC | - | Wolverhampton Wanderers | 0:2 | ||||
5. Round | 30/08/1998 | Wolverhampton Wanderers | - | Stockport County | 2:2 | ||||
7. Round | 07/09/1998 | Port Vale FC | - | Wolverhampton Wanderers | 2:1 | ||||
8. Round | 11/09/1998 | Wolverhampton Wanderers | - | Sunderland AFC | 1:1 | ||||
9. Round | 18/09/1998 | Huddersfield Town | - | Wolverhampton Wanderers | 2:1 | ||||
10. Round | 25/09/1998 | Wolverhampton Wanderers | - | Bury FC | 1:0 | ||||
11. Round | 28/09/1998 | Wolverhampton Wanderers | - | Queens Park Rangers | 1:2 | ||||
12. Round | 02/10/1998 | Crewe Alexandra | - | Wolverhampton Wanderers | 0:0 | ||||
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 |