2. Round 11/08/1999 Leicester City - Coventry City 1:0
3. Round 14/08/1999 Leicester City - Chelsea FC 2:2
4. Round 21/08/1999 West Ham United - Leicester City 2:1
7. Round 11/09/1999 Sunderland AFC - Leicester City 2:0
8. Round 18/09/1999 Leicester City - Liverpool FC 2:2
9. Round 25/09/1999 Leicester City - Aston Villa 3:1
10. Round 03/10/1999 Tottenham Hotspur - Leicester City 2:3
11. Round 16/10/1999 Leicester City - Southampton FC 2:1
12. Round 23/10/1999 Bradford City - Leicester City 3:1
13. Round 30/10/1999 Leicester City - Sheffield Wednesday 3:0
19. Round 26/12/1999 Leeds United - Leicester City 2:1
20. Round 28/12/1999 Leicester City - Newcastle United 1:2
22. Round 15/01/2000 Chelsea FC - Leicester City 1:1
23. Round 22/01/2000 Leicester City - West Ham United 1:3
24. Round 05/02/2000 Leicester City - Middlesbrough FC 2:1
25. Round 12/02/2000 Watford FC - Leicester City 1:1
28. Round 11/03/2000 Wimbledon FC - Leicester City 2:1
30. Round 26/03/2000 Leicester City - Leeds United 2:1
31. Round 02/04/2000 Derby County - Leicester City 3:0
32. Round 08/04/2000 Leicester City - Everton FC 1:1
33. Round 15/04/2000 Newcastle United - Leicester City 0:2
35. Round 19/04/2000 Leicester City - Tottenham Hotspur 0:1
34. Round 22/04/2000 Aston Villa - Leicester City 2:2
36. Round 29/04/2000 Southampton FC - Leicester City 1:2
26. Round 03/05/2000 Liverpool FC - Leicester City 0:2 Goal
37. Round 06/05/2000 Leicester City - Bradford City 3:0
38. Round 14/05/2000 Sheffield Wednesday - Leicester City 4:0