| 1. Round | 15/08/1998 | Wimbledon FC | - | Tottenham Hotspur | 3:1 | ||||
| 4. Round | 09/09/1998 | West Ham United | - | Wimbledon FC | 3:4 |  |
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| 6. Round | 19/09/1998 | Wimbledon FC | - | Sheffield Wednesday | 2:1 | ||||
| 35. Round | 24/04/1999 | Wimbledon FC | - | Newcastle United | 1:1 | ||||
| 36. Round | 01/05/1999 | Coventry City | - | Wimbledon FC | 2:1 | |
Scotland