1. Round | 07/08/1999 | Sheffield Wednesday | - | Liverpool FC | 1:2 | ||||
3. Round | 14/08/1999 | Liverpool FC | - | Watford FC | 0:1 | ||||
4. Round | 21/08/1999 | Middlesbrough FC | - | Liverpool FC | 1:0 | ||||
5. Round | 23/08/1999 | Leeds United | - | Liverpool FC | 1:2 | ||||
6. Round | 28/08/1999 | Liverpool FC | - | Arsenal FC | 2:0 | ||||
7. Round | 11/09/1999 | Liverpool FC | - | Manchester United | 2:3 | ||||
9. Round | 27/09/1999 | Liverpool FC | - | Everton FC | 0:1 | ||||
17. Round | 05/12/1999 | Liverpool FC | - | Sheffield Wednesday | 4:1 | ||||
19. Round | 26/12/1999 | Newcastle United | - | Liverpool FC | 2:2 | ||||
20. Round | 28/12/1999 | Liverpool FC | - | Wimbledon FC | 3:1 | ||||
34. Round | 21/04/2000 | Everton FC | - | Liverpool FC | 0:0 | ||||
36. Round | 29/04/2000 | Chelsea FC | - | Liverpool FC | 2:0 | ||||
26. Round | 03/05/2000 | Liverpool FC | - | Leicester City | 0:2 | ||||
37. Round | 07/05/2000 | Liverpool FC | - | Southampton FC | 0:0 |