| 4. Round | 31/08/1938 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
| 3. Round | 03/09/1938 | Aston Villa | - | Derby County | 0:1 | ||||
| 2. Round | 05/09/1938 | Aston Villa | - | Everton FC | 0:3 | ||||
| 5. Round | 10/09/1938 | Blackpool FC | - | Aston Villa | 2:4 |  |
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| 6. Round | 17/09/1938 | Aston Villa | - | Brentford FC | 5:0 | |
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| 7. Round | 24/09/1938 | Arsenal FC | - | Aston Villa | 0:0 | ||||
| 8. Round | 01/10/1938 | Aston Villa | - | Portsmouth FC | 2:0 | |
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| 9. Round | 08/10/1938 | Huddersfield Town | - | Aston Villa | 1:1 | ||||
| 10. Round | 15/10/1938 | Liverpool FC | - | Aston Villa | 3:0 | ||||
| 11. Round | 22/10/1938 | Aston Villa | - | Leicester City | 1:2 | ||||
| 13. Round | 05/11/1938 | Aston Villa | - | Manchester United | 0:2 | ||||
| 27. Round | 04/02/1939 | Portsmouth FC | - | Aston Villa | 0:0 | ||||
| 36. Round | 10/04/1939 | Wolverhampton Wanderers | - | Aston Villa | 2:1 | ||||
| 38. Round | 11/04/1939 | Aston Villa | - | Wolverhampton Wanderers | 2:2 | ||||
| 39. Round | 15/04/1939 | Aston Villa | - | Bolton Wanderers | 1:3 | ||||
| 40. Round | 22/04/1939 | Leeds United | - | Aston Villa | 2:0 |
England