| 1. Round | 02/09/1899 | Blackburn Rovers | - | Manchester City | 4:3 |  |
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| 2. Round | 09/09/1899 | Sheffield United | - | Blackburn Rovers | 3:0 | ||||
| 3. Round | 16/09/1899 | Blackburn Rovers | - | Newcastle United | 2:3 | ||||
| 4. Round | 23/09/1899 | Aston Villa | - | Blackburn Rovers | 3:1 | ||||
| 5. Round | 30/09/1899 | Blackburn Rovers | - | Liverpool FC | 2:0 | |
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| 6. Round | 07/10/1899 | Burnley FC | - | Blackburn Rovers | 1:0 | ||||
| 33. Round | 25/04/1900 | Bury FC | - | Blackburn Rovers | 2:0 | ||||
| 34. Round | 28/04/1900 | Blackburn Rovers | - | Notts County | 2:0 | ||||
| 24. Round | 30/04/1900 | Preston North End | - | Blackburn Rovers | 2:0 |
England