1. Round | 19/08/2000 | Chelsea FC | - | West Ham United | 4:2 | ||||
2. Round | 22/08/2000 | Bradford City | - | Chelsea FC | 2:0 | ||||
3. Round | 27/08/2000 | Aston Villa | - | Chelsea FC | 1:1 | ||||
4. Round | 06/09/2000 | Chelsea FC | - | Arsenal FC | 2:2 | ||||
5. Round | 09/09/2000 | Newcastle United | - | Chelsea FC | 0:0 | ||||
6. Round | 17/09/2000 | Chelsea FC | - | Leicester City | 0:2 | ||||
7. Round | 23/09/2000 | Manchester United | - | Chelsea FC | 3:3 | ||||
12. Round | 04/11/2000 | Southampton FC | - | Chelsea FC | 3:2 |