| West Ham United FC v Osijek 16/09/1999 | £5.00 | |
| Walsall FC v Manchester City FC 18/09/1999 | £8.00 | |
| Bury FC v Wycombe Wanderers FC 18/09/1999 | £5.00 | |
| Watford FC v Chelsea FC 18/09/1999 | £4.50 | |
| Fulham FC v Queens Park Rangers FC 18/09/1999 | £4.00 | |
| Fulham FC v Queens Park Rangers FC 18/09/1999 | £4.50 | |
| Aston Villa FC v Bradford City FC 18/09/1999 | £2.50 | |
| Southampton FC v Arsenal FC 18/09/1999 | £3.50 | |
| Everton FC v West Ham United FC 19/09/1999 | £5.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £4.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £5.00 | |
| Fulham FC v Norwich City FC 21/09/1999 | £4.00 |