| 2. Ronde | 09.09.1899 | Wolverhampton Wanderers | - | Nottingham Forest | 2:2 | ||||
| 3. Ronde | 16.09.1899 | Notts County | - | Wolverhampton Wanderers | 0:0 | ||||
| 19. Ronde | 18.09.1899 | Stoke City | - | Wolverhampton Wanderers | 1:3 |  |
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| 4. Ronde | 23.09.1899 | Wolverhampton Wanderers | - | Glossop North End | 4:0 | ||||
| 5. Ronde | 30.09.1899 | Manchester City | - | Wolverhampton Wanderers | 1:1 | |
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| 6. Ronde | 07.10.1899 | Wolverhampton Wanderers | - | Stoke City | 0:2 | ||||
| 23. Ronde | 03.02.1900 | Wolverhampton Wanderers | - | Manchester City | 1:1 | ||||
| 30. Ronde | 31.03.1900 | Wolverhampton Wanderers | - | Liverpool FC | 0:1 | ||||
| 24. Ronde | 17.04.1900 | Wolverhampton Wanderers | - | Sheffield United | 1:2 |
Engeland