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 | ||||
16. Round | 27/11/1999 | Coventry City | - | Leicester City | 0:1 | ||||
17. Round | 04/12/1999 | Southampton FC | - | Coventry City | 0:0 | ||||
18. Round | 18/12/1999 | Liverpool FC | - | Coventry City | 2:0 | ||||
19. Round | 26/12/1999 | Coventry City | - | Arsenal FC | 3:2 | ||||
21. Round | 04/01/2000 | Coventry City | - | Chelsea FC | 2:2 | ||||
22. Round | 15/01/2000 | Coventry City | - | Wimbledon FC | 2:0 | ||||
24. Round | 05/02/2000 | Manchester United | - | Coventry City | 3:2 | ||||
20. Round | 19/02/2000 | Middlesbrough FC | - | Coventry City | 2:0 |