1. Round | 09/08/1999 | Scunthorpe United | - | Huddersfield Town | 0:2 | ||||
1. Round | 23/08/1999 | Huddersfield Town | - | Scunthorpe United | 0:0 | ||||
2. Round | 13/09/1999 | Huddersfield Town | - | Notts County | 2:1 | ||||
2. Round | 20/09/1999 | Notts County | - | Huddersfield Town | 2:2 | ||||
3. Round | 12/10/1999 | Chelsea FC | - | Huddersfield Town | 0:1 | ||||
Round of 16 | 29/11/1999 | Huddersfield Town | - | Wimbledon FC | 1:2 aet |