| 1. Round | 27/08/1938 | Middlesbrough FC | - | Manchester United | 3:1 | ||||
| 2. Round | 31/08/1938 | Manchester United | - | Bolton Wanderers | 2:2 | ||||
| 3. Round | 03/09/1938 | Manchester United | - | Birmingham FC | 4:1 | ||||
| 4. Round | 07/09/1938 | Liverpool FC | - | Manchester United | 1:0 | ||||
| 5. Round | 10/09/1938 | Grimsby Town | - | Manchester United | 1:0 | ||||
| 6. Round | 17/09/1938 | Stoke City | - | Manchester United | 1:1 | ||||
| 7. Round | 24/09/1938 | Manchester United | - | Chelsea FC | 5:1 | ||||
| 8. Round | 01/10/1938 | Preston North End | - | Manchester United | 1:1 | ||||
| 9. Round | 08/10/1938 | Manchester United | - | Charlton Athletic | 0:2 | ||||
| 10. Round | 15/10/1938 | Manchester United | - | Blackpool FC | 0:0 | ||||
| 11. Round | 22/10/1938 | Derby County | - | Manchester United | 5:1 | ||||
| 15. Round | 19/11/1938 | Everton FC | - | Manchester United | 3:0 |
England