| Gillingham FC v York City FC 16/01/1999 | View match | |
| York City FC v Reading FC 23/01/1999 | View match | |
| York City FC v Oldham Athletic FC 30/01/1999 | View match | |
| Colchester United FC v York City FC 05/02/1999 | View match | |
| York City FC v Walsall FC 13/02/1999 | View match | |
| Wrexham FC v York City FC 20/02/1999 | View match | |
| York City FC v Fulham FC 27/02/1999 | View match | |
| Bristol Rovers FC v York City FC 06/03/1999 | View match | |
| Notts County FC v York City FC 13/03/1999 | View match | |
| York City FC v Wigan Athletic FC 20/03/1999 | View match | |
| Lincoln City FC v York City FC 28/03/1999 | View match | |
| York City FC v Chesterfield FC 03/04/1999 | View match |