2. Round | 10/08/1999 | Derby County | - | Arsenal FC | 1:2 | ||||
4. Round | 21/08/1999 | Coventry City | - | Derby County | 2:0 | ||||
8. Round | 18/09/1999 | Derby County | - | Sunderland AFC | 0:5 | ||||
9. Round | 25/09/1999 | Derby County | - | Bradford City | 0:1 | ||||
10. Round | 04/10/1999 | Southampton FC | - | Derby County | 3:3 |