| 29. Round | 18/02/1939 | Wolverhampton Wanderers | - | Leeds United | 4:1 | ||||
| 28. Round | 22/02/1939 | Wolverhampton Wanderers | - | Everton FC | 7:0 | ||||
| 30. Round | 25/02/1939 | Liverpool FC | - | Wolverhampton Wanderers | 0:2 | ||||
| 33. Round | 18/03/1939 | Wolverhampton Wanderers | - | Manchester United | 3:0 | ||||
| 35. Round | 01/04/1939 | Wolverhampton Wanderers | - | Chelsea FC | 2:0 | ||||
| 37. Round | 08/04/1939 | Preston North End | - | Wolverhampton Wanderers | 4:2 | ||||
| 41. Round | 04/05/1939 | Leicester City | - | Wolverhampton Wanderers | 0:2 | ||||
| 42. Round | 06/05/1939 | Wolverhampton Wanderers | - | Sunderland AFC | 0:0 |
England