| 2. Round | 27/09/1988 | Barnsley FC | - | Wimbledon FC | 0:2 | ||||
| 2. Round | 12/10/1988 | Wimbledon FC | - | Barnsley FC | 0:1 | ||||
| 3. Round | 01/11/1988 | Wimbledon FC | - | Manchester United | 2:1 | ||||
| Round of 16 | 29/11/1988 | Queens Park Rangers | - | Wimbledon FC | 0:0 | ||||
| Round of 16 | 13/12/1988 | Wimbledon FC | - | Queens Park Rangers | 0:1 |
Singapore