1. Round | 07/08/1999 | Portsmouth FC | - | Sheffield United | 2:0 | ||||
2. Round | 14/08/1999 | Wolverhampton Wanderers | - | Portsmouth FC | 1:1 | ||||
3. Round | 21/08/1999 | Portsmouth FC | - | Stockport County | 2:0 | ||||
4. Round | 28/08/1999 | Barnsley FC | - | Portsmouth FC | 6:0 | ||||
5. Round | 30/08/1999 | Portsmouth FC | - | Huddersfield Town | 0:0 | ||||
7. Round | 11/09/1999 | Portsmouth FC | - | Ipswich Town | 1:1 | ||||
8. Round | 18/09/1999 | Tranmere Rovers | - | Portsmouth FC | 2:4 | ||||
9. Round | 25/09/1999 | Portsmouth FC | - | Grimsby Town | 1:2 | ||||
10. Round | 02/10/1999 | Crystal Palace | - | Portsmouth FC | 4:0 | ||||
18. Round | 14/11/1999 | West Bromwich Albion | - | Portsmouth FC | 3:2 |