| Port Vale FC v Queens Park Rangers FC 01/05/1999 | £6.50 | |
| Bury FC v Port Vale FC 09/05/1999 | £5.00 | |
| Blackburn Rovers FC v Port Vale FC 07/08/1999 | View match | |
| Chester City FC v Port Vale FC 10/08/1999 | View match | |
| Port Vale FC v West Bromwich Albion FC 14/08/1999 | View match | |
| 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 | £5.00 | |
| 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 |