| 1. Round | 27/08/1938 | Leeds United | - | Preston North End | 2:1 | ||||
| 2. Round | 31/08/1938 | Leeds United | - | Birmingham FC | 2:0 | ||||
| 3. Round | 03/09/1938 | Charlton Athletic | - | Leeds United | 2:0 | ||||
| 5. Round | 10/09/1938 | Leeds United | - | Bolton Wanderers | 1:2 | ||||
| 6. Round | 17/09/1938 | Huddersfield Town | - | Leeds United | 0:1 | ||||
| 7. Round | 24/09/1938 | Liverpool FC | - | Leeds United | 3:0 | ||||
| 8. Round | 01/10/1938 | Leeds United | - | Leicester City | 8:2 | ||||
| 12. Round | 29/10/1938 | Leeds United | - | Portsmouth FC | 2:2 | ||||
| 13. Round | 05/11/1938 | Arsenal FC | - | Leeds United | 2:3 | ||||
| 14. Round | 12/11/1938 | Leeds United | - | Brentford FC | 3:2 | ||||
| 15. Round | 19/11/1938 | Blackpool FC | - | Leeds United | 1:2 | ||||
| 16. Round | 26/11/1938 | Leeds United | - | Derby County | 1:4 | ||||
| 17. Round | 03/12/1938 | Grimsby Town | - | Leeds United | 3:2 | ||||
| 19. Round | 17/12/1938 | Aston Villa | - | Leeds United | 2:1 | ||||
| 20. Round | 24/12/1938 | Preston North End | - | Leeds United | 2:0 | ||||
| 39. Round | 15/04/1939 | Sunderland AFC | - | Leeds United | 2:1 |
Northern Ireland