| 27. Round | 11/03/1899 | Preston North End | - | Liverpool FC | 1:2 | ||||
| 22. Round | 20/03/1899 | Preston North End | - | Notts County | 2:0 | ||||
| 30. Round | 01/04/1899 | Derby County | - | Preston North End | 1:0 | ||||
| 32. Round | 08/04/1899 | Preston North End | - | West Bromwich Albion | 4:0 |  |
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| 33. Round | 15/04/1899 | Blackburn Rovers | - | Preston North End | 2:2 | ||||
| 34. Round | 22/04/1899 | Preston North End | - | The Wednesday FC | 1:1 | |
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| 29. Round | 29/04/1899 | Preston North End | - | Bolton Wanderers | 0:1 |
Ireland
All Ireland