3. Round | 14/08/1999 | Leicester City | - | Chelsea FC | 2:2 | ||||
8. Round | 18/09/1999 | Watford FC | - | Chelsea FC | 1:0 | ||||
10. Round | 03/10/1999 | Chelsea FC | - | Manchester United | 5:0 | ||||
13. Round | 30/10/1999 | Derby County | - | Chelsea FC | 3:1 | ||||
15. Round | 20/11/1999 | Everton FC | - | Chelsea FC | 1:1 | ||||
16. Round | 28/11/1999 | Chelsea FC | - | Bradford City | 1:0 | ||||
17. Round | 04/12/1999 | Sunderland AFC | - | Chelsea FC | 4:1 | ||||
18. Round | 19/12/1999 | Chelsea FC | - | Leeds United | 0:2 | ||||
23. Round | 22/01/2000 | Aston Villa | - | Chelsea FC | 0:0 |