1. Round | 08/08/1999 | Manchester City | - | Wolverhampton Wanderers | 0:1 | ||||
3. Round | 21/08/1999 | Queens Park Rangers | - | Wolverhampton Wanderers | 1:1 | ||||
4. Round | 28/08/1999 | Wolverhampton Wanderers | - | Walsall FC | 1:2 | ||||
8. Round | 19/09/1999 | Nottingham Forest | - | Wolverhampton Wanderers | 1:1 | ||||
9. Round | 25/09/1999 | Sheffield United | - | Wolverhampton Wanderers | 3:0 | ||||
5. Round | 28/09/1999 | Crystal Palace | - | Wolverhampton Wanderers | 1:1 | ||||
11. Round | 09/10/1999 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:0 | ||||
12. Round | 16/10/1999 | Barnsley FC | - | Wolverhampton Wanderers | 1:2 | ||||
13. Round | 19/10/1999 | Fulham FC | - | Wolverhampton Wanderers | 0:1 | ||||
16. Round | 31/10/1999 | West Bromwich Albion | - | Wolverhampton Wanderers | 1:1 | ||||
17. Round | 06/11/1999 | Wolverhampton Wanderers | - | Grimsby Town | 3:0 | ||||
19. Round | 20/11/1999 | Wolverhampton Wanderers | - | Swindon Town | 1:1 | ||||
22. Round | 03/12/1999 | Wolverhampton Wanderers | - | Manchester City | 4:1 | ||||
6. Round | 11/01/2000 | Wolverhampton Wanderers | - | Charlton Athletic | 2:3 | ||||
33. Round | 26/02/2000 | Wolverhampton Wanderers | - | Nottingham Forest | 3:0 |