| 17. Round | 23/12/1899 | Bury FC | - | Derby County | 1:1 | ||||
| 19. Round | 25/12/1899 | Derby County | - | Liverpool FC | 3:2 |  |
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| 10. Round | 26/12/1899 | Derby County | - | Glossop North End | 4:1 | ||||
| 18. Round | 30/12/1899 | Notts County | - | Derby County | 0:0 | ||||
| 20. Round | 06/01/1900 | Derby County | - | Manchester City | 0:0 | ||||
| 21. Round | 13/01/1900 | Sheffield United | - | Derby County | 1:1 | ||||
| 22. Round | 20/01/1900 | Derby County | - | Newcastle United | 2:1 |
Scotland