| 1. Round | 27/08/1938 | Birmingham FC | - | Sunderland AFC | 1:2 |  |
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| 3. Round | 03/09/1938 | Sunderland AFC | - | Grimsby Town | 1:1 | ||||
| 12. Round | 29/10/1938 | Manchester United | - | Sunderland AFC | 0:1 | ||||
| 13. Round | 05/11/1938 | Sunderland AFC | - | Stoke City | 3:0 | ||||
| 14. Round | 12/11/1938 | Chelsea FC | - | Sunderland AFC | 4:0 | ||||
| 15. Round | 19/11/1938 | Sunderland AFC | - | Preston North End | 1:2 | |
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| 22. Round | 27/12/1938 | Aston Villa | - | Sunderland AFC | 1:1 | |
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| 29. Round | 18/02/1939 | Sunderland AFC | - | Leicester City | 2:0 |
England