| 3. Round | 16/09/1899 | Derby County | - | Sheffield United | 0:1 | ||||
| 4. Round | 23/09/1899 | Newcastle United | - | Derby County | 2:0 | ||||
| 5. Round | 30/09/1899 | Derby County | - | Aston Villa | 2:0 | ||||
| 6. Round | 07/10/1899 | Liverpool FC | - | Derby County | 0:2 | ||||
| 7. Round | 14/10/1899 | Derby County | - | Burnley FC | 4:1 | ||||
| 8. Round | 21/10/1899 | Preston North End | - | Derby County | 0:0 | ||||
| 9. Round | 28/10/1899 | Derby County | - | Nottingham Forest | 2:2 | ||||
| 11. Round | 11/11/1899 | Derby County | - | Stoke City | 2:0 | ||||
| 13. Round | 25/11/1899 | Derby County | - | West Bromwich Albion | 4:1 |  |
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| 14. Round | 02/12/1899 | Everton FC | - | Derby County | 3:0 |
England