7. Round | 11/09/1999 | Liverpool FC | - | Manchester United | 2:3 | ||||
8. Round | 18/09/1999 | Manchester United | - | Wimbledon FC | 1:1 | ||||
9. Round | 25/09/1999 | Manchester United | - | Southampton FC | 3:3 | ||||
10. Round | 03/10/1999 | Chelsea FC | - | Manchester United | 5:0 |