| 18. Round | 10/12/1938 | Leeds United | - | Sunderland AFC | 3:3 | ||||
| 19. Round | 17/12/1938 | Sunderland AFC | - | Liverpool FC | 2:3 | ||||
| 32. Round | 11/03/1939 | Stoke City | - | Sunderland AFC | 3:1 | ||||
| 28. Round | 15/03/1939 | Sunderland AFC | - | Portsmouth FC | 0:2 | ||||
| 33. Round | 18/03/1939 | Sunderland AFC | - | Chelsea FC | 3:2 | ||||
| 34. Round | 25/03/1939 | Preston North End | - | Sunderland AFC | 2:1 | ||||
| 42. Round | 06/05/1939 | Wolverhampton Wanderers | - | Sunderland AFC | 0:0 |
England