| Ipswich Town FC v Portsmouth FC 26/12/1998 | View match | |
| Portsmouth FC v Oxford United FC 28/12/1998 | View match | |
| Nottingham Forest FC v Portsmouth FC 02/01/1999 | View match | |
| Watford FC v Portsmouth FC 09/01/1999 | View match | |
| Portsmouth FC v Huddersfield Town FC 16/01/1999 | £5.00 | |
| Portsmouth FC v Leeds United FC 23/01/1999 | View match | |
| Queens Park Rangers FC v Portsmouth FC 30/01/1999 | View match | |
| Portsmouth FC v Tranmere Rovers FC 06/02/1999 | View match | |
| 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 |