7. Round | 11/09/1999 | Coventry City | - | Leeds United | 3:4 | ||||
8. Round | 19/09/1999 | Tottenham Hotspur | - | Coventry City | 3:2 | ||||
9. Round | 25/09/1999 | Coventry City | - | West Ham United | 1:0 | ||||
10. Round | 02/10/1999 | Everton FC | - | Coventry City | 1:1 | ||||
11. Round | 16/10/1999 | Coventry City | - | Newcastle United | 4:1 | ||||
12. Round | 23/10/1999 | Sheffield Wednesday | - | Coventry City | 0:0 | ||||
13. Round | 31/10/1999 | Coventry City | - | Watford FC | 4:0 | ||||
14. Round | 06/11/1999 | Bradford City | - | Coventry City | 1:1 | ||||
15. Round | 22/11/1999 | Coventry City | - | Aston Villa | 2:1 |