| Luton Town FC v York City FC 06/04/1999 | £4.00 | |
| York City FC v Millwall FC 10/04/1999 | View match | |
| Northampton Town FC v York City FC 13/04/1999 | View match | |
| York City FC v Stoke City FC 17/04/1999 | View match | |
| Macclesfield Town FC v York City FC 24/04/1999 | View match | |
| 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 |