| 1. Round | 21/08/1948 | Sunderland AFC | - | Bolton Wanderers | 2:0 | ||||
| 2. Round | 25/08/1948 | Bolton Wanderers | - | Aston Villa | 3:0 | ||||
| 3. Round | 28/08/1948 | Bolton Wanderers | - | Wolverhampton Wanderers | 0:5 | ||||
| 4. Round | 30/08/1948 | Aston Villa | - | Bolton Wanderers | 2:4 | ||||
| 5. Round | 04/09/1948 | Chelsea FC | - | Bolton Wanderers | 2:2 | ||||
| 6. Round | 06/09/1948 | Bolton Wanderers | - | Huddersfield Town | 1:2 | ||||
| 7. Round | 11/09/1948 | Liverpool FC | - | Bolton Wanderers | 0:1 | ||||
| 8. Round | 15/09/1948 | Huddersfield Town | - | Bolton Wanderers | 0:2 | ||||
| 9. Round | 18/09/1948 | Bolton Wanderers | - | Blackpool FC | 2:2 | ||||
| 10. Round | 25/09/1948 | Derby County | - | Bolton Wanderers | 1:0 | ||||
| 11. Round | 02/10/1948 | Bolton Wanderers | - | Arsenal FC | 1:0 | ||||
| 12. Round | 09/10/1948 | Bolton Wanderers | - | Birmingham City | 0:0 | ||||
| 13. Round | 16/10/1948 | Middlesbrough FC | - | Bolton Wanderers | 5:0 | ||||
| 14. Round | 23/10/1948 | Bolton Wanderers | - | Newcastle United | 1:5 | ||||
| 35. Round | 02/04/1949 | Manchester City | - | Bolton Wanderers | 1:0 |
England