| 1er tour | 10.08.1999 | Scunthorpe United | - | Huddersfield Town | 0:2 |  |
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| 2e tour | 21.09.1999 | Notts County | - | Huddersfield Town | 2:2 | ||||
| 3e tour | 13.10.1999 | Chelsea FC | - | Huddersfield Town | 0:1 |  |
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| tour des 16 | 30.11.1999 | Huddersfield Town | - | Wimbledon FC | 1:2 ap |
Angleterre