| 1. Round | 08/08/1999 | Manchester City | - | Wolverhampton Wanderers | 0:1 | ||||
| 3. Round | 21/08/1999 | Queens Park Rangers | - | Wolverhampton Wanderers | 1:1 |  |
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| 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 |  |
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| 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 |
Australia
