1. Round | 07/08/1999 | Chelsea FC | - | Sunderland AFC | 4:0 | ||||
13. Round | 30/10/1999 | Derby County | - | Chelsea FC | 3:1 | ||||
15. Round | 20/11/1999 | Everton FC | - | Chelsea FC | 1:1 | ||||
18. Round | 19/12/1999 | Chelsea FC | - | Leeds United | 0:2 | ||||
19. Round | 26/12/1999 | Southampton FC | - | Chelsea FC | 1:2 | ||||
20. Round | 29/12/1999 | Chelsea FC | - | Sheffield Wednesday | 3:0 | ||||
21. Round | 04/01/2000 | Coventry City | - | Chelsea FC | 2:2 | ||||
2. Round | 08/01/2000 | Bradford City | - | Chelsea FC | 1:1 | ||||
5. Round | 12/01/2000 | Chelsea FC | - | Tottenham Hotspur | 1:0 | ||||
22. Round | 15/01/2000 | Chelsea FC | - | Leicester City | 1:1 | ||||
27. Round | 04/03/2000 | Newcastle United | - | Chelsea FC | 0:1 | ||||
28. Round | 11/03/2000 | Chelsea FC | - | Everton FC | 1:1 | ||||
29. Round | 18/03/2000 | West Ham United | - | Chelsea FC | 0:0 | ||||
31. Round | 01/04/2000 | Leeds United | - | Chelsea FC | 0:1 | ||||
32. Round | 12/04/2000 | Chelsea FC | - | Coventry City | 2:1 | ||||
36. Round | 29/04/2000 | Chelsea FC | - | Liverpool FC | 2:0 | ||||
37. Round | 06/05/2000 | Arsenal FC | - | Chelsea FC | 2:1 | ||||
38. Round | 14/05/2000 | Chelsea FC | - | Derby County | 4:0 |