| AFC Bournemouth v Cardiff City FC 06/11/1999 | View match | |
| Cardiff City FC v Leyton Orient FC 09/11/1999 | View match | |
| Cardiff City FC v Chesterfield FC 12/11/1999 | View match | |
| Bury FC v Cardiff City FC 20/11/1999 | £6.50 | |
| Colchester United FC v Cardiff City FC 23/11/1999 | View match | |
| Cardiff City FC v Gillingham FC 27/11/1999 | View match | |
| Cardiff City FC v Bury FC 30/11/1999 | £4.00 | |
| Millwall FC v Cardiff City FC 04/12/1999 | View match | |
| Burnley FC v Cardiff City FC 18/12/1999 | View match | |
| Bolton Wanderers FC v Cardiff City FC 21/12/1999 | View match | |
| Cardiff City FC v Reading FC 26/12/1999 | View match | |
| Cambridge United FC v Cardiff City FC 28/12/1999 | View match |