3. Ronde | 14.08.1999 | Leicester City | - | Chelsea FC | 2:2 | ||||
4. Ronde | 21.08.1999 | Chelsea FC | - | Aston Villa | 1:0 | ||||
7. Ronde | 11.09.1999 | Chelsea FC | - | Newcastle United | 1:0 | ||||
8. Ronde | 18.09.1999 | Watford FC | - | Chelsea FC | 1:0 | ||||
16. Ronde | 28.11.1999 | Chelsea FC | - | Bradford City | 1:0 | ||||
17. Ronde | 04.12.1999 | Sunderland AFC | - | Chelsea FC | 4:1 |