| Crystal Palace FC v Portsmouth FC 02/10/1999 | View match | |
| Portsmouth FC v Charlton Athletic FC 16/10/1999 | View match | |
| Portsmouth FC v Walsall FC 19/10/1999 | £2.50 | |
| Queens Park Rangers FC v Portsmouth FC 23/10/1999 | View match | |
| Grimsby Town FC v Portsmouth FC 26/10/1999 | View match | |
| Portsmouth FC v Crystal Palace FC 30/10/1999 | View match | |
| Manchester City FC v Portsmouth FC 03/11/1999 | £5.00 | |
| Portsmouth FC v Birmingham City FC 06/11/1999 | View match | |
| Fulham FC v Portsmouth FC 09/11/1999 | £4.50 | |
| West Bromwich Albion FC v Portsmouth FC 14/11/1999 | View match | |
| Portsmouth FC v Crewe Alexandra FC 20/11/1999 | View match | |
| Nottingham Forest FC v Portsmouth FC 24/11/1999 | View match |