| 1. Round | 02/09/1899 | West Bromwich Albion | - | Newcastle United | 1:1 | ||||
| 2. Round | 09/09/1899 | Aston Villa | - | West Bromwich Albion | 0:2 | ||||
| 3. Round | 16/09/1899 | West Bromwich Albion | - | Liverpool FC | 2:0 | ||||
| 4. Round | 23/09/1899 | Burnley FC | - | West Bromwich Albion | 2:0 | ||||
| 9. Round | 28/10/1899 | West Bromwich Albion | - | Sunderland AFC | 1:0 | ||||
| 10. Round | 04/11/1899 | Wolverhampton Wanderers | - | West Bromwich Albion | 2:0 | ||||
| 34. Round | 06/11/1899 | West Bromwich Albion | - | Sheffield United | 1:2 | ||||
| 11. Round | 11/11/1899 | Everton FC | - | West Bromwich Albion | 1:3 | ||||
| 14. Round | 02/12/1899 | West Bromwich Albion | - | Bury FC | 0:1 | ||||
| 15. Round | 09/12/1899 | Notts County | - | West Bromwich Albion | 1:2 | ||||
| 17. Round | 23/12/1899 | Sheffield United | - | West Bromwich Albion | 1:1 | ||||
| 20. Round | 06/01/1900 | West Bromwich Albion | - | Aston Villa | 0:2 | ||||
| 21. Round | 13/01/1900 | Liverpool FC | - | West Bromwich Albion | 2:0 |
England