| Arsenal FC v Derby County FC 02/05/1999 | £2.00 | |
| Leicester City FC v Derby County FC 05/05/1999 | View match | |
| Derby County FC v Coventry City FC 08/05/1999 | View match | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.00 | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.50 | |
| Leeds United FC v Derby County FC 07/08/1999 | View match | |
| Derby County FC v Arsenal FC 10/08/1999 | £3.50 | |
| Derby County FC v Middlesbrough FC 14/08/1999 | View match | |
| Coventry City FC v Derby County FC 21/08/1999 | View match | |
| Sheffield Wednesday FC v Derby County FC 25/08/1999 | £4.00 | |
| Derby County FC v Everton FC 28/08/1999 | View match | |
| Wimbledon v Derby County FC 11/09/1999 | View match |