| 1. Round | 27/08/1938 | Middlesbrough FC | - | Manchester United | 3:1 | ||||
| 2. Round | 31/08/1938 | Manchester United | - | Bolton Wanderers | 2:2 | ||||
| 6. Round | 17/09/1938 | Stoke City | - | Manchester United | 1:1 | ||||
| 11. Round | 22/10/1938 | Derby County | - | Manchester United | 5:1 | ||||
| 12. Round | 29/10/1938 | Manchester United | - | Sunderland AFC | 0:1 | ||||
| 15. Round | 19/11/1938 | Everton FC | - | Manchester United | 3:0 | ||||
| 35. Round | 01/04/1939 | Huddersfield Town | - | Manchester United | 1:1 | ||||
| 36. Round | 07/04/1939 | Manchester United | - | Leeds United | 0:0 | ||||
| 37. Round | 08/04/1939 | Manchester United | - | Portsmouth FC | 1:1 | ||||
| 38. Round | 10/04/1939 | Leeds United | - | Manchester United | 3:1 | ||||
| 39. Round | 15/04/1939 | Arsenal FC | - | Manchester United | 2:1 | ||||
| 40. Round | 22/04/1939 | Manchester United | - | Brentford FC | 3:0 | ||||
| 41. Round | 29/04/1939 | Bolton Wanderers | - | Manchester United | 0:0 | ||||
| 42. Round | 06/05/1939 | Manchester United | - | Liverpool FC | 2:0 |
England