| York City FC v Blackpool FC 27/04/1999 | View match | |
| York City FC v AFC Bournemouth 01/05/1999 | View match | |
| Manchester City FC v York City FC 08/05/1999 | £6.00 | |
| York City FC v Swansea City FC 07/08/1999 | View match | |
| York City FC v Wigan Athletic FC 10/08/1999 | View match | |
| Torquay United FC v York City FC 14/08/1999 | View match | |
| York City FC v Rochdale FC 21/08/1999 | View match | |
| Wigan Athletic FC v York City FC 24/08/1999 | View match | |
| Barnet FC v York City FC 28/08/1999 | View match | |
| York City FC v Northampton Town FC 30/08/1999 | View match | |
| Rotherham United FC v York City FC 04/09/1999 | View match | |
| York City FC v Peterborough United FC 11/09/1999 | View match |