| Port Vale FC v Grimsby Town FC 23/03/1999 | View match | |
| Bristol City FC v Port Vale FC 03/04/1999 | View match | |
| Port Vale FC v Barnsley FC 05/04/1999 | View match | |
| Crewe Alexandra FC v Port Vale FC 10/04/1999 | View match | |
| Port Vale FC v Bradford City FC 13/04/1999 | View match | |
| Port Vale FC v Oxford United FC 17/04/1999 | View match | |
| Tranmere Rovers FC v Port Vale FC 24/04/1999 | View match | |
| Port Vale FC v Watford FC 27/04/1999 | View match | |
| Port Vale FC v Queens Park Rangers FC 01/05/1999 | View match | |
| 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 |