1. Round | 07/08/1998 | Portsmouth FC | - | Watford FC | 1:2 | ||||
3. Round | 21/08/1998 | Portsmouth FC | - | Ipswich Town | 0:0 | ||||
4. Round | 28/08/1998 | Huddersfield Town | - | Portsmouth FC | 3:3 | ||||
5. Round | 30/08/1998 | Portsmouth FC | - | Queens Park Rangers | 3:0 | ||||
6. Round | 05/09/1998 | Oxford United | - | Portsmouth FC | 3:0 | ||||
7. Round | 07/09/1998 | Bury FC | - | Portsmouth FC | 2:1 | ||||
8. Round | 11/09/1998 | Portsmouth FC | - | Swindon Town | 5:2 | ||||
9. Round | 18/09/1998 | Port Vale FC | - | Portsmouth FC | 0:2 | ||||
10. Round | 25/09/1998 | Portsmouth FC | - | Sunderland AFC | 1:1 | ||||
11. Round | 28/09/1998 | Portsmouth FC | - | Birmingham City | 0:1 | ||||
12. Round | 02/10/1998 | Sheffield United | - | Portsmouth FC | 2:1 | ||||
13. Round | 09/10/1998 | Bristol City | - | Portsmouth FC | 2:2 | ||||
32. Round | 19/02/1999 | Swindon Town | - | Portsmouth FC | 3:3 |