| 3. Round | 17/09/1898 | Nottingham Forest | - | Sunderland AFC | 1:1 | ||||
| 4. Round | 24/09/1898 | Sunderland AFC | - | Bolton Wanderers | 0:0 | ||||
| 12. Round | 19/11/1898 | Notts County | - | Sunderland AFC | 5:2 | ||||
| 13. Round | 26/11/1898 | Sunderland AFC | - | Stoke City | 2:0 | ||||
| 15. Round | 10/12/1898 | Sunderland AFC | - | Burnley FC | 0:1 | ||||
| 19. Round | 02/01/1899 | Sunderland AFC | - | Derby County | 1:0 | ||||
| 20. Round | 07/01/1899 | Liverpool FC | - | Sunderland AFC | 0:0 | ||||
| 21. Round | 14/01/1899 | Sunderland AFC | - | Nottingham Forest | 1:1 |  |
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| 22. Round | 21/01/1899 | Bolton Wanderers | - | Sunderland AFC | 6:1 |
Scotland