| 1. Ronde | 08.08.1999 | Manchester City | - | Wolverhampton Wanderers | 0:1 | ||||
| 3. Ronde | 21.08.1999 | Queens Park Rangers | - | Wolverhampton Wanderers | 1:1 |  |
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| 4. Ronde | 28.08.1999 | Wolverhampton Wanderers | - | Walsall FC | 1:2 | ||||
| 8. Ronde | 19.09.1999 | Nottingham Forest | - | Wolverhampton Wanderers | 1:1 | ||||
| 9. Ronde | 25.09.1999 | Sheffield United | - | Wolverhampton Wanderers | 3:0 | ||||
| 5. Ronde | 28.09.1999 | Crystal Palace | - | Wolverhampton Wanderers | 1:1 | ||||
| 11. Ronde | 09.10.1999 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:0 | ||||
| 12. Ronde | 16.10.1999 | Barnsley FC | - | Wolverhampton Wanderers | 1:2 |  |
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| 13. Ronde | 19.10.1999 | Fulham FC | - | Wolverhampton Wanderers | 0:1 | ||||
| 16. Ronde | 31.10.1999 | West Bromwich Albion | - | Wolverhampton Wanderers | 1:1 | ||||
| 17. Ronde | 06.11.1999 | Wolverhampton Wanderers | - | Grimsby Town | 3:0 | ||||
| 19. Ronde | 20.11.1999 | Wolverhampton Wanderers | - | Swindon Town | 1:1 | ||||
| 22. Ronde | 03.12.1999 | Wolverhampton Wanderers | - | Manchester City | 4:1 | ||||
| 6. Ronde | 11.01.2000 | Wolverhampton Wanderers | - | Charlton Athletic | 2:3 | ||||
| 33. Ronde | 26.02.2000 | Wolverhampton Wanderers | - | Nottingham Forest | 3:0 |
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