| 17. Round | 26/12/1898 | Derby County | - | Bolton Wanderers | 1:1 | ||||
| 18. Round | 31/12/1898 | Bury FC | - | Derby County | 0:0 | ||||
| 19. Round | 02/01/1899 | Sunderland AFC | - | Derby County | 1:0 | ||||
| 20. Round | 07/01/1899 | Derby County | - | West Bromwich Albion | 4:1 |  |
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| 21. Round | 14/01/1899 | Blackburn Rovers | - | Derby County | 3:0 | ||||
| 22. Round | 21/01/1899 | Derby County | - | The Wednesday FC | 9:0 | |
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| 23. Round | 04/02/1899 | Derby County | - | Wolverhampton Wanderers | 6:2 | |
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| 24. Round | 18/02/1899 | Derby County | - | Notts County | 4:2 | ||||
| 26. Round | 04/03/1899 | Derby County | - | Aston Villa | 1:1 | ||||
| 27. Round | 11/03/1899 | Burnley FC | - | Derby County | 2:1 | ||||
| 29. Round | 25/03/1899 | Newcastle United | - | Derby County | 2:0 | ||||
| 34. Round | 31/03/1899 | Bolton Wanderers | - | Derby County | 2:1 | ||||
| 30. Round | 01/04/1899 | Derby County | - | Preston North End | 1:0 | ||||
| 31. Round | 03/04/1899 | Everton FC | - | Derby County | 1:2 | ||||
| 32. Round | 08/04/1899 | Liverpool FC | - | Derby County | 4:0 | ||||
| 33. Round | 20/04/1899 | Derby County | - | Nottingham Forest | 2:0 |
Scotland