| 2e tour | 14.09.1999 | Cardiff City | - | Wimbledon FC | 1:1 | ||||
| 2e tour | 21.09.1999 | Wimbledon FC | - | Cardiff City | 3:1 | ||||
| 3e tour | 12.10.1999 | Wimbledon FC | - | Sunderland AFC | 3:2 ap | ||||
| tour des 16 | 30.11.1999 | Huddersfield Town | - | Wimbledon FC | 1:2 ap |  |
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| Quarts de finale | 14.12.1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 |
Angleterre