| Sheffield Wednesday FC v Derby County FC 30/01/1999 | £2.50 | |
| Tottenham Hotspur FC v Derby County FC 27/02/1999 | £2.00 | |
| Tottenham Hotspur FC v Derby County FC 27/02/1999 | £4.50 | |
| Arsenal FC v Derby County FC 02/05/1999 | £2.00 | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.00 | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.50 | |
| Derby County FC v Arsenal FC 10/08/1999 | £3.50 | |
| Sheffield Wednesday FC v Derby County FC 25/08/1999 | £4.00 | |
| Southampton FC v Derby County FC 04/10/1999 | £2.50 | |
| Southampton FC v Derby County FC 04/10/1999 | £3.50 | |
| Derby County FC v Tottenham Hotspur FC 16/10/1999 | £4.00 | |
| Derby County FC v Chelsea FC 30/10/1999 | £6.50 |