1. Round | 12/08/2000 | Sheffield United | - | Portsmouth FC | 2:0 | ||||
3. Round | 25/08/2000 | Gillingham FC | - | Portsmouth FC | 1:1 | ||||
4. Round | 28/08/2000 | Portsmouth FC | - | Wolverhampton Wanderers | 3:1 | ||||
5. Round | 02/09/2000 | Preston North End | - | Portsmouth FC | 1:0 |