13. Round | 30/10/1999 | Derby County | - | Chelsea FC | 3:1 | ||||
17. Round | 04/12/1999 | Sunderland AFC | - | Chelsea FC | 4:1 | ||||
18. Round | 19/12/1999 | Chelsea FC | - | Leeds United | 0:2 | ||||
19. Round | 26/12/1999 | Southampton FC | - | Chelsea FC | 1:2 | ||||
5. Round | 12/01/2000 | Chelsea FC | - | Tottenham Hotspur | 1:0 | ||||
22. Round | 15/01/2000 | Chelsea FC | - | Leicester City | 1:1 | ||||
23. Round | 22/01/2000 | Aston Villa | - | Chelsea FC | 0:0 | ||||
24. Round | 05/02/2000 | Tottenham Hotspur | - | Chelsea FC | 0:1 | ||||
25. Round | 12/02/2000 | Chelsea FC | - | Wimbledon FC | 3:1 | ||||
26. Round | 26/02/2000 | Chelsea FC | - | Watford FC | 2:1 | ||||
28. Round | 11/03/2000 | Chelsea FC | - | Everton FC | 1:1 | ||||
30. Round | 25/03/2000 | Chelsea FC | - | Southampton FC | 1:1 | ||||
31. Round | 01/04/2000 | Leeds United | - | Chelsea FC | 0:1 | ||||
32. Round | 12/04/2000 | Chelsea FC | - | Coventry City | 2:1 | ||||
34. Round | 22/04/2000 | Chelsea FC | - | Middlesbrough FC | 1:1 | ||||
35. Round | 24/04/2000 | Manchester United | - | Chelsea FC | 3:2 | ||||
36. Round | 29/04/2000 | Chelsea FC | - | Liverpool FC | 2:0 |