| Charlton Athletic FC v Norwich City FC 21/08/1999 | £4.00 | |
| West Ham United FC v Leicester City FC 21/08/1999 | £5.00 | |
| Manchester City FC v Sheffield United FC 21/08/1999 | £5.00 | |
| Queens Park Rangers FC v Wolverhampton Wanderers FC 21/08/1999 | £4.50 | |
| 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 |