| Southampton FC v Leeds United FC 11/08/1999 | £3.50 | |
| Aston Villa FC v Everton FC 11/08/1999 | £2.00 | |
| Tottenham Hotspur FC v Everton FC 14/08/1999 | £5.00 | |
| Wrexham FC v Bury FC 14/08/1999 | £7.50 | |
| Leyton Orient FC v Brighton & Hove Albion FC 14/08/1999 | £7.50 | |
| Luton Town FC v Blackpool FC 14/08/1999 | £5.00 | |
| Fulham FC v Manchester City FC 14/08/1999 | £4.00 | |
| Leicester City FC v Chelsea FC 14/08/1999 | £3.50 | |
| Southampton FC v Newcastle United FC 15/08/1999 | £3.00 | |
| Southampton FC v Newcastle United FC 15/08/1999 | £3.50 | |
| Aston Villa FC v West Ham United FC 16/08/1999 | £2.50 | |
| Aston Villa FC v West Ham United FC 16/08/1999 | £4.00 |