| Portsmouth FC v Bury FC 13/02/1999 | View match | |
| Swindon Town FC v Portsmouth FC 20/02/1999 | View match | |
| Portsmouth FC v Port Vale FC 27/02/1999 | View match | |
| Sunderland FC v Portsmouth FC 02/03/1999 | View match | |
| Birmingham City FC v Portsmouth FC 06/03/1999 | View match | |
| Portsmouth FC v Sheffield United FC 09/03/1999 | View match | |
| Portsmouth FC v Crystal Palace FC 13/03/1999 | View match | |
| Norwich City FC v Portsmouth FC 20/03/1999 | View match | |
| Portsmouth FC v Barnsley FC 28/03/1999 | £6.50 | |
| Wolverhampton Wanderers FC v Portsmouth FC 03/04/1999 | View match | |
| Portsmouth FC v Bristol City FC 05/04/1999 | View match | |
| Bradford City FC v Portsmouth FC 10/04/1999 | View match |