| 3. Round | 07/01/1990 | Nottingham Forest | - | Manchester United | 0:1 | ||||
| 4. Round | 27/01/1990 | Hereford United | - | Manchester United | 0:1 | ||||
| Round of 16 | 17/02/1990 | Newcastle United | - | Manchester United | 2:3 | ||||
| Quarter-finals | 10/03/1990 | Sheffield United | - | Manchester United | 0:1 | ||||
| Semi-finals | 08/04/1990 | Manchester United | - | Oldham Athletic | 3:3 aet | ||||
| Semi-finals | 11/04/1990 | Manchester United | - | Oldham Athletic | 2:1 aet | ||||
| Final | 12/05/1990 | Manchester United | - | Crystal Palace | 3:3 aet |
Scotland