| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £3.00 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £2.50 | |
| Leeds United FC v Arsenal FC 11/05/1999 | £4.00 | |
| West Ham (Youth) v Coventry City (Youth) 14/05/1999 | £4.50 | |
| Kingstonian FC v Forest Green Rovers 15/05/1999 | £9.00 | |
| West Ham United FC v Middlesbrough FC 16/05/1999 | £5.00 | |
| Arsenal FC v Aston Villa FC 16/05/1999 | £3.50 | |
| Arsenal FC v Aston Villa FC 16/05/1999 | £2.50 | |
| Charlton Athletic FC v Sheffield Wednesday FC 16/05/1999 | £3.00 | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.00 | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.50 |