| 3. Runde | 11.12.1999 | Sheffield Wednesday | - | Bristol City | 1:0 | ||||
| 4. Runde | 08.01.2000 | Sheffield Wednesday | - | Wolverhampton Wanderers | 1:1 |  |
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| 4. Runde | 18.01.2000 | Wolverhampton Wanderers | - | Sheffield Wednesday | 3:4 i.E. | ||||
| Achtelfinale | 29.01.2000 | Gillingham FC | - | Sheffield Wednesday | 3:1 |  |
Niederlande