| West Ham United FC v Leicester City FC 21/08/1999 | £5.00 | |
| Bury FC v Brentford FC 21/08/1999 | £6.00 | |
| Crystal Palace FC v Swindon Town FC 21/08/1999 | £2.00 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £6.50 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £3.00 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £3.50 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £4.00 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £2.50 | |
| Arsenal FC v Manchester United FC 22/08/1999 | £3.00 | |
| Arsenal FC v Manchester United FC 22/08/1999 | £6.00 | |
| Wolverhampton Wanderers FC v Wycombe Wanderers FC 24/08/1999 | £4.50 | |
| Fulham FC v Northampton Town FC 24/08/1999 | £4.00 |