| 2. Round | 22/08/1989 | Derby County | - | Wimbledon FC | 1:1 | ||||
| 11. Round | 28/10/1989 | Sheffield Wednesday | - | Wimbledon FC | 0:1 | ||||
| 12. Round | 03/11/1989 | Wimbledon FC | - | Queens Park Rangers | 0:0 | ||||
| 14. Round | 17/11/1989 | Everton FC | - | Wimbledon FC | 1:1 | ||||
| 15. Round | 24/11/1989 | Wimbledon FC | - | Aston Villa | 0:2 | ||||
| 22. Round | 12/01/1990 | Wimbledon FC | - | Arsenal FC | 1:0 | ||||
| 23. Round | 19/01/1990 | Millwall FC | - | Wimbledon FC | 0:0 | ||||
| 25. Round | 09/02/1990 | Manchester City | - | Wimbledon FC | 1:1 | ||||
| 24. Round | 13/02/1990 | Wimbledon FC | - | Luton Town | 1:2 | ||||
| 27. Round | 23/02/1990 | Aston Villa | - | Wimbledon FC | 0:3 | ||||
| 28. Round | 02/03/1990 | Wimbledon FC | - | Everton FC | 3:1 | ||||
| 30. Round | 16/03/1990 | Wimbledon FC | - | Southampton FC | 3:3 | ||||
| 26. Round | 01/05/1990 | Wimbledon FC | - | Crystal Palace | 0:1 |
Ireland