| 2. Round | 13/09/1999 | Cardiff City | - | Wimbledon FC | 1:1 | ||||
| 3. Round | 11/10/1999 | Wimbledon FC | - | Sunderland AFC | 3:2 aet | ||||
| Round of 16 | 29/11/1999 | Huddersfield Town | - | Wimbledon FC | 1:2 aet | ||||
| Quarter-finals | 13/12/1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 |
| 2. Round | 13/09/1999 | Cardiff City | - | Wimbledon FC | 1:1 | ||||
| 3. Round | 11/10/1999 | Wimbledon FC | - | Sunderland AFC | 3:2 aet | ||||
| Round of 16 | 29/11/1999 | Huddersfield Town | - | Wimbledon FC | 1:2 aet | ||||
| Quarter-finals | 13/12/1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 |
| Carl Winston Leaburn | |
| Born: | 30.03.1969 |
| Place of birth: |
Lewisham, 
England |
| Nationality: |
England
|
| Height: | 191 cm |
| Weight: | 83 kg |
| Position(s): | Centre Forward |