| 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 | |
| Port Vale FC v Crystal Palace FC 20/11/1999 | View match | |
| Sheffield United FC v Port Vale FC 23/11/1999 | View match | |
| 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 |