1. Round | 07/08/1999 | Coventry City | - | Southampton FC | 0:1 | ||||
2. Round | 11/08/1999 | Leicester City | - | Coventry City | 1:0 | ||||
3. Round | 14/08/1999 | Wimbledon FC | - | Coventry City | 1:1 | ||||
4. Round | 21/08/1999 | Coventry City | - | Derby County | 2:0 | ||||
8. Round | 19/09/1999 | Tottenham Hotspur | - | Coventry City | 3:2 | ||||
15. Round | 22/11/1999 | Coventry City | - | Aston Villa | 2:1 | ||||
16. Round | 27/11/1999 | Coventry City | - | Leicester City | 0:1 | ||||
20. Round | 19/02/2000 | Middlesbrough FC | - | Coventry City | 2:0 | ||||
26. Round | 26/02/2000 | Coventry City | - | Tottenham Hotspur | 0:1 | ||||
27. Round | 05/03/2000 | Leeds United | - | Coventry City | 3:0 | ||||
28. Round | 11/03/2000 | Aston Villa | - | Coventry City | 1:0 | ||||
35. Round | 15/03/2000 | Coventry City | - | Everton FC | 1:0 | ||||
32. Round | 12/04/2000 | Chelsea FC | - | Coventry City | 2:1 | ||||
33. Round | 15/04/2000 | Coventry City | - | Middlesbrough FC | 2:1 | ||||
34. Round | 22/04/2000 | West Ham United | - | Coventry City | 5:0 |