| Port Vale FC v Fulham FC 11/09/1999 | View match | |
| Stockport County FC v Port Vale FC 18/09/1999 | View match | |
| Port Vale FC v Swindon Town FC 25/09/1999 | View match | |
| Manchester City FC v Port Vale FC 02/10/1999 | £4.00 | |
| Huddersfield Town FC v Port Vale FC 09/10/1999 | View match | |
| Port Vale FC v Norwich City FC 16/10/1999 | View match | |
| Port Vale FC v Nottingham Forest FC 19/10/1999 | View match | |
| Wolverhampton Wanderers FC v Port Vale FC 23/10/1999 | View match | |
| Swindon Town FC v Port Vale FC 26/10/1999 | View match | |
| Port Vale FC v Manchester City FC 30/10/1999 | View match | |
| Port Vale FC v Crewe Alexandra FC 05/11/1999 | View match | |
| Walsall FC v Port Vale FC 12/11/1999 | View match |