| 3. Round | 10/12/1999 | Sheffield Wednesday | - | Bristol City | 1:0 | ||||
| 4. Round | 07/01/2000 | Sheffield Wednesday | - | Wolverhampton Wanderers | 1:1 |  |
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| 4. Round | 17/01/2000 | Wolverhampton Wanderers | - | Sheffield Wednesday | 3:4 pso | ||||
| Round of 16 | 28/01/2000 | Gillingham FC | - | Sheffield Wednesday | 3:1 |  |
Netherlands