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
8. Round 18/09/1999 Leicester City - Liverpool FC 2:2
9. Round 27/09/1999 Liverpool FC - Everton FC 0:1
10. Round 02/10/1999 Aston Villa - Liverpool FC 0:0
11. Round 16/10/1999 Liverpool FC - Chelsea FC 1:0
12. Round 23/10/1999 Southampton FC - Liverpool FC 1:1
2. Round 27/10/1999 Liverpool FC - West Ham United 1:0 yellow card
13. Round 01/11/1999 Liverpool FC - Bradford City 3:1 yellow card
14. Round 06/11/1999 Liverpool FC - Derby County 2:0
17. Round 05/12/1999 Liverpool FC - Sheffield Wednesday 4:1
18. Round 18/12/1999 Liverpool FC - Coventry City 2:0
19. Round 26/12/1999 Newcastle United - Liverpool FC 2:2
20. Round 28/12/1999 Liverpool FC - Wimbledon FC 3:1
21. Round 03/01/2000 Tottenham Hotspur - Liverpool FC 1:0 yellow card
22. Round 15/01/2000 Watford FC - Liverpool FC 2:3
23. Round 22/01/2000 Liverpool FC - Middlesbrough FC 0:0
24. Round 05/02/2000 Liverpool FC - Leeds United 3:1
25. Round 13/02/2000 Arsenal FC - Liverpool FC 0:1
27. Round 04/03/2000 Manchester United - Liverpool FC 1:1
28. Round 11/03/2000 Liverpool FC - Sunderland AFC 1:1 yellow card
35. Round 15/03/2000 Liverpool FC - Aston Villa 0:0
29. Round 18/03/2000 Derby County - Liverpool FC 0:2
30. Round 25/03/2000 Liverpool FC - Newcastle United 2:1
31. Round 01/04/2000 Coventry City - Liverpool FC 0:3
32. Round 09/04/2000 Liverpool FC - Tottenham Hotspur 2:0
33. Round 16/04/2000 Wimbledon FC - Liverpool FC 1:2
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
38. Round 14/05/2000 Bradford City - Liverpool FC 1:0