| 1. Round | 08/08/1999 | Manchester City | - | Wolverhampton Wanderers | 0:1 | ||||
| 3. Round | 21/08/1999 | Queens Park Rangers | - | Wolverhampton Wanderers | 1:1 | ||||
| 7. Round | 11/09/1999 | Wolverhampton Wanderers | - | Huddersfield Town | 0:1 | ||||
| 8. Round | 19/09/1999 | Nottingham Forest | - | Wolverhampton Wanderers | 1:1 | ||||
| 9. Round | 25/09/1999 | Sheffield United | - | Wolverhampton Wanderers | 3:0 | ||||
| 11. Round | 09/10/1999 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:0 | ||||
| 12. Round | 16/10/1999 | Barnsley FC | - | Wolverhampton Wanderers | 1:2 | ||||
| 17. Round | 06/11/1999 | Wolverhampton Wanderers | - | Grimsby Town | 3:0 | ||||
| 24. Round | 26/12/1999 | Stockport County | - | Wolverhampton Wanderers | 3:2 | ||||
| 25. Round | 28/12/1999 | Wolverhampton Wanderers | - | Norwich City | 1:0 | ||||
| 26. Round | 03/01/2000 | Blackburn Rovers | - | Wolverhampton Wanderers | 1:1 | ||||
| 31. Round | 12/02/2000 | Charlton Athletic | - | Wolverhampton Wanderers | 2:0 | ||||
| 32. Round | 16/02/2000 | Wolverhampton Wanderers | - | Tranmere Rovers | 4:0 | ||||
| 35. Round | 07/03/2000 | Grimsby Town | - | Wolverhampton Wanderers | 1:0 |
England