| 1. Round | 20/08/1949 | West Bromwich Albion | - | Charlton Athletic | 1:0 | ||||
| 2. Round | 24/08/1949 | Birmingham City | - | West Bromwich Albion | 2:0 | ||||
| 3. Round | 27/08/1949 | Manchester United | - | West Bromwich Albion | 1:1 | ||||
| 4. Round | 31/08/1949 | West Bromwich Albion | - | Birmingham City | 3:0 |  |
|||
| 5. Round | 03/09/1949 | West Bromwich Albion | - | Chelsea FC | 1:1 | ||||
| 6. Round | 07/09/1949 | West Bromwich Albion | - | Arsenal FC | 1:2 | ||||
| 7. Round | 10/09/1949 | Stoke City | - | West Bromwich Albion | 1:3 | |
|||
| 8. Round | 14/09/1949 | Arsenal FC | - | West Bromwich Albion | 4:1 | ||||
| 9. Round | 17/09/1949 | West Bromwich Albion | - | Burnley FC | 3:0 | ||||
| 10. Round | 24/09/1949 | Sunderland AFC | - | West Bromwich Albion | 2:1 | ||||
| 11. Round | 01/10/1949 | West Bromwich Albion | - | Liverpool FC | 0:1 |
England