| 1. Round | 27/08/1938 | Middlesbrough FC | - | Manchester United | 3:1 | ||||
| 13. Round | 05/11/1938 | Aston Villa | - | Manchester United | 0:2 | ||||
| 32. Round | 11/03/1939 | Manchester United | - | Aston Villa | 1:1 | ||||
| 33. Round | 18/03/1939 | Wolverhampton Wanderers | - | Manchester United | 3:0 | ||||
| 34. Round | 29/03/1939 | Manchester United | - | Everton FC | 0:2 | ||||
| 35. Round | 01/04/1939 | Huddersfield Town | - | Manchester United | 1:1 |
Ireland