| 1. Round | 01/09/1900 | Bolton Wanderers | - | Derby County | 0:1 | ||||
| 2. Round | 08/09/1900 | The Wednesday FC | - | Bolton Wanderers | 1:0 | ||||
| 3. Round | 15/09/1900 | Notts County | - | Bolton Wanderers | 3:1 | ||||
| 4. Round | 22/09/1900 | Bolton Wanderers | - | Preston North End | 1:1 | ||||
| 5. Round | 29/09/1900 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:1 | ||||
| 7. Round | 13/10/1900 | Liverpool FC | - | Bolton Wanderers | 2:1 | ||||
| 8. Round | 20/10/1900 | Bolton Wanderers | - | Newcastle United | 3:2 | ||||
| 9. Round | 27/10/1900 | Sheffield United | - | Bolton Wanderers | 0:2 | ||||
| 10. Round | 03/11/1900 | Bolton Wanderers | - | Manchester City | 0:0 | ||||
| 11. Round | 10/11/1900 | Bury FC | - | Bolton Wanderers | 3:0 | ||||
| 31. Round | 12/11/1900 | Stoke City | - | Bolton Wanderers | 2:1 | ||||
| 13. Round | 24/11/1900 | Blackburn Rovers | - | Bolton Wanderers | 2:0 |
Scotland