| York City FC v Lincoln City FC 21/03/2000 | View match | |
| York City FC v Hartlepool United 25/03/2000 | View match | |
| Southend United FC v York City FC 01/04/2000 | View match | |
| York City FC v Darlington FC 08/04/2000 | View match | |
| Cheltenham Town FC v York City FC 15/04/2000 | View match | |
| York City FC v Brighton & Hove Albion FC 22/04/2000 | £5.50 | |
| Chester City FC v York City FC 24/04/2000 | View match | |
| York City FC v Halifax Town A.F.C 29/04/2000 | View match | |
| Leyton Orient FC v York City FC 06/05/2000 | View match | |
| York City FC v Manchester United FC 29/07/2000 | View match | |
| York City FC v Middlesbrough FC 01/08/2000 | View match | |
| Chesterfield FC v York City FC 12/08/2000 | View match |