1. Round | 19/08/2000 | Chelsea FC | - | West Ham United | 4:2 | ||||
2. Round | 22/08/2000 | Bradford City | - | Chelsea FC | 2:0 | ||||
8. Round | 01/10/2000 | Chelsea FC | - | Liverpool FC | 3:0 | ||||
9. Round | 14/10/2000 | Sunderland AFC | - | Chelsea FC | 1:0 | ||||
10. Round | 21/10/2000 | Chelsea FC | - | Coventry City | 6:1 | ||||
11. Round | 28/10/2000 | Chelsea FC | - | Tottenham Hotspur | 3:0 | ||||
12. Round | 04/11/2000 | Southampton FC | - | Chelsea FC | 3:2 | ||||
13. Round | 12/11/2000 | Chelsea FC | - | Leeds United | 1:1 | ||||
14. Round | 18/11/2000 | Charlton Athletic | - | Chelsea FC | 2:0 | ||||
15. Round | 25/11/2000 | Everton FC | - | Chelsea FC | 2:1 | ||||
16. Round | 03/12/2000 | Chelsea FC | - | Manchester City | 2:1 | ||||
17. Round | 09/12/2000 | Chelsea FC | - | Derby County | 4:1 | ||||
18. Round | 16/12/2000 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
19. Round | 23/12/2000 | Chelsea FC | - | Bradford City | 3:0 | ||||
20. Round | 26/12/2000 | Ipswich Town | - | Chelsea FC | 2:2 |