| 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 | ||||
| 15. Round | 30/10/1948 | Portsmouth FC | - | Bolton Wanderers | 0:0 | ||||
| 16. Round | 06/11/1948 | Bolton Wanderers | - | Manchester City | 5:1 | ||||
| 17. Round | 13/11/1948 | Charlton Athletic | - | Bolton Wanderers | 1:4 | ||||
| 18. Round | 20/11/1948 | Bolton Wanderers | - | Stoke City | 2:1 | ||||
| 19. Round | 27/11/1948 | Burnley FC | - | Bolton Wanderers | 3:0 | ||||
| 20. Round | 04/12/1948 | Bolton Wanderers | - | Preston North End | 5:3 | ||||
| 21. Round | 11/12/1948 | Everton FC | - | Bolton Wanderers | 1:0 | ||||
| 27. Round | 22/01/1949 | Bolton Wanderers | - | Liverpool FC | 0:3 | ||||
| 30. Round | 26/02/1949 | Arsenal FC | - | Bolton Wanderers | 5:0 | ||||
| 32. Round | 12/03/1949 | Bolton Wanderers | - | Middlesbrough FC | 4:1 | ||||
| 40. Round | 23/04/1949 | Bolton Wanderers | - | Portsmouth FC | 1:2 | ||||
| 41. Round | 30/04/1949 | Preston North End | - | Bolton Wanderers | 1:1 | ||||
| 26. Round | 04/05/1949 | Bolton Wanderers | - | Chelsea FC | 1:1 | ||||
| 42. Round | 07/05/1949 | Bolton Wanderers | - | Everton FC | 1:0 |
England