| 19. Round | 17/12/1938 | Sunderland AFC | - | Liverpool FC | 2:3 | ||||
| 20. Round | 24/12/1938 | Sunderland AFC | - | Birmingham FC | 1:0 | ||||
| 21. Round | 26/12/1938 | Sunderland AFC | - | Aston Villa | 1:5 | ||||
| 22. Round | 27/12/1938 | Aston Villa | - | Sunderland AFC | 1:1 | ||||
| 23. Round | 31/12/1938 | Grimsby Town | - | Sunderland AFC | 1:3 |  |
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| 24. Round | 14/01/1939 | Sunderland AFC | - | Derby County | 1:0 | ||||
| 25. Round | 25/01/1939 | Blackpool FC | - | Sunderland AFC | 1:1 | ||||
| 26. Round | 28/01/1939 | Sunderland AFC | - | Brentford FC | 1:1 | ||||
| 27. Round | 04/02/1939 | Arsenal FC | - | Sunderland AFC | 2:0 | ||||
| 30. Round | 25/02/1939 | Middlesbrough FC | - | Sunderland AFC | 3:0 | ||||
| 37. Round | 08/04/1939 | Bolton Wanderers | - | Sunderland AFC | 2:1 |
England