| 16. Round | 26/11/1938 | Bolton Wanderers | - | Grimsby Town | 1:1 | ||||
| 20. Round | 24/12/1938 | Charlton Athletic | - | Bolton Wanderers | 2:1 | ||||
| 22. Round | 27/12/1938 | Preston North End | - | Bolton Wanderers | 2:2 | ||||
| 23. Round | 31/12/1938 | Bolton Wanderers | - | Portsmouth FC | 5:1 | ||||
| 36. Round | 02/01/1939 | Bolton Wanderers | - | Stoke City | 1:3 | ||||
| 24. Round | 14/01/1939 | Bolton Wanderers | - | Leeds United | 2:2 | ||||
| 28. Round | 22/02/1939 | Bolton Wanderers | - | Birmingham FC | 3:0 | ||||
| 30. Round | 25/02/1939 | Bolton Wanderers | - | Huddersfield Town | 3:2 | ||||
| 35. Round | 01/04/1939 | Grimsby Town | - | Bolton Wanderers | 1:1 | ||||
| 37. Round | 08/04/1939 | Bolton Wanderers | - | Sunderland AFC | 2:1 | ||||
| 38. Round | 10/04/1939 | Stoke City | - | Bolton Wanderers | 4:1 | ||||
| 39. Round | 15/04/1939 | Aston Villa | - | Bolton Wanderers | 1:3 | ||||
| 40. Round | 22/04/1939 | Bolton Wanderers | - | Wolverhampton Wanderers | 0:0 | ||||
| 21. Round | 26/04/1939 | Bolton Wanderers | - | Preston North End | 0:2 | ||||
| 41. Round | 29/04/1939 | Bolton Wanderers | - | Manchester United | 0:0 | ||||
| 42. Round | 06/05/1939 | Chelsea FC | - | Bolton Wanderers | 1:1 |
England