| Charlton Athletic FC v Port Vale FC 27/11/1999 | £4.50 | |
| Port Vale FC v Blackburn Rovers FC 04/12/1999 | View match | |
| Leeds United FC v Port Vale FC 12/12/1999 | View match | |
| Portsmouth FC v Port Vale FC 18/12/1999 | View match | |
| Barnsley FC v Port Vale FC 28/12/1999 | View match | |
| Port Vale FC v Ipswich Town FC 03/01/2000 | View match | |
| West Bromwich Albion FC v Port Vale FC 15/01/2000 | View match | |
| Port Vale FC v Birmingham City FC 22/01/2000 | View match | |
| Port Vale FC v Queens Park Rangers FC 05/02/2000 | View match | |
| Port Vale FC v Bolton Wanderers FC 08/02/2000 | View match | |
| Grimsby Town FC v Port Vale FC 12/02/2000 | View match | |
| Port Vale FC v Stockport County FC 26/02/2000 | View match |