3. Round | 14/08/1999 | Leicester City | - | Chelsea FC | 2:2 | ||||
4. Round | 21/08/1999 | Chelsea FC | - | Aston Villa | 1:0 | ||||
7. Round | 11/09/1999 | Chelsea FC | - | Newcastle United | 1:0 | ||||
8. Round | 18/09/1999 | Watford FC | - | Chelsea FC | 1:0 | ||||
16. Round | 28/11/1999 | Chelsea FC | - | Bradford City | 1:0 | ||||
17. Round | 04/12/1999 | Sunderland AFC | - | Chelsea FC | 4:1 |