1. Round | 16/08/1999 | Torquay United | - | Portsmouth FC | 0:0 | ||||
1. Round | 23/08/1999 | Portsmouth FC | - | Torquay United | 3:0 | ||||
2. Round | 21/09/1999 | Blackburn Rovers | - | Portsmouth FC | 3:1 |
1. Round | 16/08/1999 | Torquay United | - | Portsmouth FC | 0:0 | ||||
1. Round | 23/08/1999 | Portsmouth FC | - | Torquay United | 3:0 | ||||
2. Round | 21/09/1999 | Blackburn Rovers | - | Portsmouth FC | 3:1 |