| 3. Round | 02/01/1999 | Manchester United | - | Middlesbrough FC | 3:1 |  |
|||
| 4. Round | 23/01/1999 | Manchester United | - | Liverpool FC | 2:1 | ||||
| Round of 16 | 13/02/1999 | Manchester United | - | Fulham FC | 1:0 | |
|||
| Quarter-finals | 06/03/1999 | Manchester United | - | Chelsea FC | 0:0 | ||||
| Quarter-finals | 09/03/1999 | Chelsea FC | - | Manchester United | 0:2 | ||||
| Semi-finals | 10/04/1999 | Manchester United | - | Arsenal FC | 0:0 aet | ||||
| Final | 22/05/1999 | Manchester United | - | Newcastle United | 2:0 |
England
