| 2. Round | 17/09/1989 | Port Vale FC | - | Wimbledon FC | 1:2 | ||||
| 2. Round | 04/10/1989 | Wimbledon FC | - | Port Vale FC | 3:0 | ||||
| 3. Round | 25/10/1989 | Middlesbrough FC | - | Wimbledon FC | 1:1 | ||||
| 3. Round | 07/11/1989 | Wimbledon FC | - | Middlesbrough FC | 1:0 | ||||
| Round of 16 | 21/11/1989 | West Ham United | - | Wimbledon FC | 1:0 |
England