| 1. Ronde | 02.09.1899 | Bury FC | - | Wolverhampton Wanderers | 3:0 | ||||
| 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 | ||||
| 21. Ronde | 13.01.1900 | Wolverhampton Wanderers | - | Notts County | 2:2 | ||||
| 22. Ronde | 20.01.1900 | Glossop North End | - | Wolverhampton Wanderers | 2:3 | ||||
| 28. Ronde | 16.04.1900 | Wolverhampton Wanderers | - | Aston Villa | 0:1 | ||||
| 24. Ronde | 17.04.1900 | Wolverhampton Wanderers | - | Sheffield United | 1:2 | ||||
| 34. Ronde | 28.04.1900 | Preston North End | - | Wolverhampton Wanderers | 2:0 |
Wales