1. Round | 07/08/1999 | Coventry City | - | Southampton FC | 0:1 | ||||
2. Round | 11/08/1999 | Leicester City | - | Coventry City | 1:0 | ||||
4. Round | 21/08/1999 | Coventry City | - | Derby County | 2:0 | ||||
5. Round | 25/08/1999 | Coventry City | - | Manchester United | 1:2 | ||||
6. Round | 29/08/1999 | Sunderland AFC | - | Coventry City | 1:1 | ||||
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 |