| 16. Round | 17/12/1898 | Sheffield United | - | Sunderland AFC | 2:0 | ||||
| 17. Round | 24/12/1898 | Wolverhampton Wanderers | - | Sheffield United | 4:1 | ||||
| 32. Round | 26/12/1898 | Sheffield United | - | The Wednesday FC | 2:1 | ||||
| 18. Round | 31/12/1898 | Everton FC | - | Sheffield United | 1:0 | ||||
| 25. Round | 02/01/1899 | Sheffield United | - | Liverpool FC | 0:2 | ||||
| 20. Round | 07/01/1899 | Sheffield United | - | Notts County | 2:2 | ||||
| 21. Round | 14/01/1899 | Stoke City | - | Sheffield United | 4:1 | ||||
| 22. Round | 21/01/1899 | Sheffield United | - | Aston Villa | 1:3 | ||||
| 23. Round | 04/02/1899 | Sheffield United | - | Bury FC | 4:1 | ||||
| 24. Round | 18/02/1899 | Preston North End | - | Sheffield United | 1:0 | ||||
| 26. Round | 04/03/1899 | Nottingham Forest | - | Sheffield United | 2:1 | ||||
| 27. Round | 11/03/1899 | Sheffield United | - | Bolton Wanderers | 3:1 | ||||
| 29. Round | 25/03/1899 | Sheffield United | - | West Bromwich Albion | 5:0 | ||||
| 19. Round | 31/03/1899 | Burnley FC | - | Sheffield United | 1:0 | ||||
| 30. Round | 01/04/1899 | Blackburn Rovers | - | Sheffield United | 2:1 | ||||
| 33. Round | 29/04/1899 | Sunderland AFC | - | Sheffield United | 1:0 |
Ireland
All Ireland