| 1. Round | 20/08/1949 | Bolton Wanderers | - | Stoke City | 4:0 | ||||
| 2. Round | 24/08/1949 | Manchester United | - | Bolton Wanderers | 3:0 | ||||
| 3. Round | 27/08/1949 | Burnley FC | - | Bolton Wanderers | 2:1 | ||||
| 4. Round | 31/08/1949 | Bolton Wanderers | - | Manchester United | 1:2 | ||||
| 5. Round | 03/09/1949 | Bolton Wanderers | - | Sunderland AFC | 2:1 | ||||
| 6. Round | 05/09/1949 | Bolton Wanderers | - | Derby County | 0:0 | ||||
| 7. Round | 10/09/1949 | Liverpool FC | - | Bolton Wanderers | 1:1 | ||||
| 10. Round | 24/09/1949 | Portsmouth FC | - | Bolton Wanderers | 1:1 | ||||
| 11. Round | 01/10/1949 | Birmingham City | - | Bolton Wanderers | 0:0 | ||||
| 12. Round | 08/10/1949 | Bolton Wanderers | - | Huddersfield Town | 1:2 | ||||
| 13. Round | 15/10/1949 | Everton FC | - | Bolton Wanderers | 0:0 | ||||
| 14. Round | 22/10/1949 | Bolton Wanderers | - | Middlesbrough FC | 1:2 | ||||
| 18. Round | 19/11/1949 | Bolton Wanderers | - | Manchester City | 3:0 | ||||
| 19. Round | 26/11/1949 | Charlton Athletic | - | Bolton Wanderers | 0:0 | ||||
| 20. Round | 03/12/1949 | Bolton Wanderers | - | Aston Villa | 1:1 | ||||
| 21. Round | 10/12/1949 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:1 | ||||
| 22. Round | 17/12/1949 | Stoke City | - | Bolton Wanderers | 3:2 |
England