| 1. Round | 02/09/1899 | Stoke City | - | Liverpool FC | 3:2 | ||||
| 2. Round | 09/09/1899 | Liverpool FC | - | Sunderland AFC | 0:2 | ||||
| 3. Round | 16/09/1899 | West Bromwich Albion | - | Liverpool FC | 2:0 | ||||
| 6. Round | 07/10/1899 | Liverpool FC | - | Derby County | 0:2 | ||||
| 7. Round | 14/10/1899 | Bury FC | - | Liverpool FC | 2:1 | ||||
| 8. Round | 21/10/1899 | Liverpool FC | - | Notts County | 3:1 | ||||
| 9. Round | 28/10/1899 | Manchester City | - | Liverpool FC | 0:1 | ||||
| 10. Round | 04/11/1899 | Liverpool FC | - | Sheffield United | 2:2 | ||||
| 11. Round | 11/11/1899 | Newcastle United | - | Liverpool FC | 1:1 | ||||
| 12. Round | 18/11/1899 | Liverpool FC | - | Aston Villa | 3:3 | ||||
| 13. Round | 25/11/1899 | Liverpool FC | - | Wolverhampton Wanderers | 1:1 | ||||
| 14. Round | 02/12/1899 | Burnley FC | - | Liverpool FC | 2:1 | ||||
| 15. Round | 09/12/1899 | Liverpool FC | - | Preston North End | 1:0 |
England