| 16. Round | 17/12/1898 | Bolton Wanderers | - | Bury FC | 0:1 | ||||
| 17. Round | 26/12/1898 | Derby County | - | Bolton Wanderers | 1:1 | ||||
| 18. Round | 31/12/1898 | West Bromwich Albion | - | Bolton Wanderers | 1:0 | ||||
| 26. Round | 03/01/1899 | Bolton Wanderers | - | Burnley FC | 2:0 | ||||
| 20. Round | 07/01/1899 | Bolton Wanderers | - | Blackburn Rovers | 0:2 |
Scotland