1. Round | 02/09/1899 | Bury FC | - | Wolverhampton Wanderers | 3:0 | ||||
2. Round | 09/09/1899 | Wolverhampton Wanderers | - | Nottingham Forest | 2:2 | ||||
3. Round | 16/09/1899 | Notts County | - | Wolverhampton Wanderers | 0:0 | ||||
19. Round | 18/09/1899 | Stoke City | - | Wolverhampton Wanderers | 1:3 | ||||
4. Round | 23/09/1899 | Wolverhampton Wanderers | - | Glossop North End | 4:0 | ||||
7. Round | 14/10/1899 | Sheffield United | - | Wolverhampton Wanderers | 5:2 | ||||
9. Round | 28/10/1899 | Newcastle United | - | Wolverhampton Wanderers | 0:1 | ||||
10. Round | 04/11/1899 | Wolverhampton Wanderers | - | West Bromwich Albion | 2:0 | ||||
11. Round | 11/11/1899 | Aston Villa | - | Wolverhampton Wanderers | 0:0 | ||||
21. Round | 13/01/1900 | Wolverhampton Wanderers | - | Notts County | 2:2 | ||||
23. Round | 03/02/1900 | Wolverhampton Wanderers | - | Manchester City | 1:1 |