| Cardiff City FC v Wimbledon 14/09/1999 | View match | |
| Cardiff City FC v Notts County FC 18/09/1999 | View match | |
| Wimbledon v Cardiff City FC 21/09/1999 | View match | |
| Cardiff City FC v Wigan Athletic FC 25/09/1999 | View match | |
| Brentford FC v Cardiff City FC 28/09/1999 | View match | |
| Bury FC v Cardiff City FC 02/10/1999 | £6.00 | |
| Bristol Rovers FC v Cardiff City FC 09/10/1999 | View match | |
| Cardiff City FC v Oldham Athletic FC 16/10/1999 | View match | |
| Cardiff City FC v Stoke City FC 19/10/1999 | View match | |
| Wigan Athletic FC v Cardiff City FC 23/10/1999 | View match | |
| Leyton Orient FC v Cardiff City FC 30/10/1999 | View match | |
| Cardiff City FC v Blackpool FC 02/11/1999 | View match |