| 4. Round | 07/09/1938 | Sunderland AFC | - | Wolverhampton Wanderers | 1:1 | ||||
| 5. Round | 10/09/1938 | Derby County | - | Sunderland AFC | 1:0 | ||||
| 2. Round | 14/09/1938 | Huddersfield Town | - | Sunderland AFC | 0:1 | ||||
| 20. Round | 24/12/1938 | Sunderland AFC | - | Birmingham FC | 1:0 | ||||
| 21. Round | 26/12/1938 | Sunderland AFC | - | Aston Villa | 1:5 | ||||
| 29. Round | 18/02/1939 | Sunderland AFC | - | Leicester City | 2:0 | ||||
| 30. Round | 25/02/1939 | Middlesbrough FC | - | Sunderland AFC | 3:0 | ||||
| 31. Round | 04/03/1939 | Sunderland AFC | - | Manchester United | 5:2 | ||||
| 32. Round | 11/03/1939 | Stoke City | - | Sunderland AFC | 3:1 | ||||
| 28. Round | 15/03/1939 | Sunderland AFC | - | Portsmouth FC | 0:2 | ||||
| 40. Round | 22/04/1939 | Liverpool FC | - | Sunderland AFC | 1:1 | ||||
| 41. Round | 29/04/1939 | Sunderland AFC | - | Huddersfield Town | 0:0 |
Scotland