| 18. Round | 18/12/1999 | Leicester City | - | Derby County | 0:1 | ||||
| 19. Round | 26/12/1999 | Leeds United | - | Leicester City | 2:1 | ||||
| 20. Round | 28/12/1999 | Leicester City | - | Newcastle United | 1:2 | ||||
| 21. Round | 03/01/2000 | Everton FC | - | Leicester City | 2:2 | ||||
| 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 | ||||
| 27. Round | 05/03/2000 | Leicester City | - | Sunderland AFC | 5:2 | ||||
| 29. Round | 18/03/2000 | Leicester City | - | Manchester United | 0:2 | ||||
| 30. Round | 26/03/2000 | Leicester City | - | Leeds United | 2:1 | ||||
| 31. Round | 02/04/2000 | Derby County | - | Leicester City | 3:0 | ||||
| 36. Round | 29/04/2000 | Southampton FC | - | Leicester City | 1:2 | ||||
| 26. Round | 03/05/2000 | Liverpool FC | - | Leicester City | 0:2 | ||||
| 37. Round | 06/05/2000 | Leicester City | - | Bradford City | 3:0 | ||||
| 38. Round | 14/05/2000 | Sheffield Wednesday | - | Leicester City | 4:0 |
England