| Luton Town FC v Wrexham FC 11/09/1999 | £6.00 | |
| Halifax Town A.F.C v Brighton & Hove Albion FC 11/09/1999 | £7.50 | |
| Manchester City FC v Crystal Palace FC 11/09/1999 | £5.00 | |
| West Ham United FC v Watford FC 11/09/1999 | £5.00 | |
| Middlesbrough FC v Southampton FC 11/09/1999 | £6.50 | |
| Oldham Athletic FC v Bury FC 11/09/1999 | £6.00 | |
| Charlton Athletic FC v Bolton Wanderers FC 11/09/1999 | £4.50 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £3.00 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £2.00 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £2.50 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £3.50 | |
| Chelsea FC v Newcastle United FC 11/09/1999 | £3.50 |