| Birmingham City FC v Port Vale FC 21/08/1999 | View match | |
| Port Vale FC v Chester City FC 24/08/1999 | View match | |
| Port Vale FC v Tranmere Rovers FC 28/08/1999 | View match | |
| Queens Park Rangers FC v Port Vale FC 31/08/1999 | View match | |
| Port Vale FC v Grimsby Town FC 05/09/1999 | View match | |
| 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 |