4. Round | 21/08/1999 | Chelsea FC | - | Aston Villa | 1:0 | ||||
6. Round | 28/08/1999 | Wimbledon FC | - | Chelsea FC | 0:1 | ||||
8. Round | 18/09/1999 | Watford FC | - | Chelsea FC | 1:0 | ||||
9. Round | 25/09/1999 | Middlesbrough FC | - | Chelsea FC | 0:1 | ||||
13. Round | 30/10/1999 | Derby County | - | Chelsea FC | 3:1 | ||||
14. Round | 07/11/1999 | Chelsea FC | - | West Ham United | 0:0 | ||||
15. Round | 20/11/1999 | Everton FC | - | Chelsea FC | 1:1 | ||||
19. Round | 26/12/1999 | Southampton FC | - | Chelsea FC | 1:2 | ||||
20. Round | 29/12/1999 | Chelsea FC | - | Sheffield Wednesday | 3:0 | ||||
22. Round | 15/01/2000 | Chelsea FC | - | Leicester City | 1:1 | ||||
30. Round | 25/03/2000 | Chelsea FC | - | Southampton FC | 1:1 | ||||
32. Round | 12/04/2000 | Chelsea FC | - | Coventry City | 2:1 | ||||
33. Round | 15/04/2000 | Sheffield Wednesday | - | Chelsea FC | 1:0 | ||||
34. Round | 22/04/2000 | Chelsea FC | - | Middlesbrough FC | 1:1 | ||||
35. Round | 24/04/2000 | Manchester United | - | Chelsea FC | 3:2 | ||||
38. Round | 14/05/2000 | Chelsea FC | - | Derby County | 4:0 |