| 1. Round | 02/09/1899 | Nottingham Forest | - | Preston North End | 3:1 |  |
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| 2. Round | 09/09/1899 | Preston North End | - | Glossop North End | 1:0 | |
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| 3. Round | 16/09/1899 | Stoke City | - | Preston North End | 3:1 | ||||
| 4. Round | 23/09/1899 | Preston North End | - | Sunderland AFC | 0:1 | ||||
| 8. Round | 21/10/1899 | Preston North End | - | Derby County | 0:0 | ||||
| 9. Round | 28/10/1899 | Bury FC | - | Preston North End | 2:0 | ||||
| 10. Round | 04/11/1899 | Preston North End | - | Notts County | 4:3 | ||||
| 11. Round | 11/11/1899 | Manchester City | - | Preston North End | 3:1 |
England