| 1. Runde | 10.08.1999 | Scunthorpe United | - | Huddersfield Town | 0:2 |  |
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| 1. Runde | 24.08.1999 | Huddersfield Town | - | Scunthorpe United | 0:0 | ||||
| 2. Runde | 14.09.1999 | Huddersfield Town | - | Notts County | 2:1 | ||||
| 2. Runde | 21.09.1999 | Notts County | - | Huddersfield Town | 2:2 | ||||
| 3. Runde | 13.10.1999 | Chelsea FC | - | Huddersfield Town | 0:1 |
England