| 3. Round | 17/09/1898 | Bolton Wanderers | - | The Wednesday FC | 0:0 | ||||
| 7. Round | 15/10/1898 | Bolton Wanderers | - | Notts County | 0:1 | ||||
| 17. Round | 26/12/1898 | Derby County | - | Bolton Wanderers | 1:1 |  |
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| 18. Round | 31/12/1898 | West Bromwich Albion | - | Bolton Wanderers | 1:0 | ||||
| 21. Round | 14/01/1899 | The Wednesday FC | - | Bolton Wanderers | 1:0 | ||||
| 22. Round | 21/01/1899 | Bolton Wanderers | - | Sunderland AFC | 6:1 | |
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| 24. Round | 18/02/1899 | Bolton Wanderers | - | Stoke City | 0:2 | ||||
| 23. Round | 25/02/1899 | Bolton Wanderers | - | Everton FC | 2:4 | |
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| 27. Round | 11/03/1899 | Sheffield United | - | Bolton Wanderers | 3:1 | ||||
| 28. Round | 18/03/1899 | Bolton Wanderers | - | Newcastle United | 0:0 | ||||
| 34. Round | 31/03/1899 | Bolton Wanderers | - | Derby County | 2:1 | |
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| 30. Round | 01/04/1899 | Bolton Wanderers | - | Liverpool FC | 2:1 | ||||
| 31. Round | 03/04/1899 | Notts County | - | Bolton Wanderers | 2:1 | ||||
| 32. Round | 08/04/1899 | Nottingham Forest | - | Bolton Wanderers | 1:2 | ||||
| 25. Round | 17/04/1899 | Bolton Wanderers | - | Aston Villa | 0:0 | ||||
| 29. Round | 29/04/1899 | Preston North End | - | Bolton Wanderers | 0:1 |
England