| Liverpool FC v Tottenham Hotspur FC 01/05/1999 | £5.00 | |
| Arsenal FC v Derby County FC 02/05/1999 | £2.00 | |
| Arsenal FC v Derby County FC 02/05/1999 | £5.00 | |
| Tottenham Hotspur FC v Arsenal FC 05/05/1999 | £4.50 | |
| Tottenham Hotspur FC v Arsenal FC 05/05/1999 | £3.00 | |
| Chelsea FC v Leeds United FC 05/05/1999 | £3.50 | |
| Chelsea FC v Leeds United FC 05/05/1999 | £3.50 | |
| Chelsea FC v Leeds United FC 05/05/1999 | £3.00 | |
| Everton FC v West Ham United FC 08/05/1999 | £5.50 | |
| Fulham FC v Preston North End FC 08/05/1999 | £3.50 | |
| Manchester City FC v York City FC 08/05/1999 | £6.00 | |
| Brighton & Hove Albion FC v Rochdale FC 08/05/1999 | £8.50 |