1. Round | 18/08/1989 | Coventry City | - | Everton FC | 2:0 | ||||
2. Round | 21/08/1989 | Arsenal FC | - | Coventry City | 2:0 | ||||
3. Round | 25/08/1989 | Crystal Palace | - | Coventry City | 0:1 | ||||
4. Round | 29/08/1989 | Coventry City | - | Manchester City | 2:1 | ||||
5. Round | 08/09/1989 | Millwall FC | - | Coventry City | 4:1 | ||||
6. Round | 15/09/1989 | Coventry City | - | Luton Town | 1:0 | ||||
9. Round | 14/10/1989 | Coventry City | - | Nottingham Forest | 0:2 | ||||
10. Round | 21/10/1989 | Coventry City | - | Manchester United | 1:4 | ||||
16. Round | 01/12/1989 | Everton FC | - | Coventry City | 2:0 | ||||
26. Round | 16/02/1990 | Coventry City | - | Millwall FC | 3:1 | ||||
28. Round | 03/03/1990 | Coventry City | - | Aston Villa | 2:0 |