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 |