| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £4.00 | |
| Southampton FC v Sheffield Wednesday FC 28/08/1999 | £3.50 | |
| Aston Villa FC v Middlesbrough FC 28/08/1999 | £2.50 | |
| Luton Town FC v Cardiff City FC 28/08/1999 | £5.00 | |
| Bradford City FC v West Ham United FC 28/08/1999 | £4.00 | |
| Fulham FC v Charlton Athletic FC 28/08/1999 | £4.00 | |
| Nottingham Forest FC v Queens Park Rangers FC 28/08/1999 | £5.00 | |
| Bristol City FC v Bury FC 28/08/1999 | £5.00 | |
| Manchester City FC v Nottingham Forest FC 30/08/1999 | £5.00 | |
| Bury FC v Colchester United FC 30/08/1999 | £4.50 | |
| Queens Park Rangers FC v Port Vale FC 31/08/1999 | £5.00 | |
| Luton Town FC v Bury FC 04/09/1999 | £4.00 |