| Chelsea FC v Newcastle United FC 11/09/1999 | £3.00 | |
| Sheffield Wednesday FC v Everton FC 11/09/1999 | £9.50 | |
| Bradford City FC v Tottenham Hotspur FC 12/09/1999 | £6.50 | |
| Charlton Athletic FC v AFC Bournemouth 14/09/1999 | £5.50 | |
| Manchester United FC v NK Croatia Zegreb 14/09/1999 | £4.80 | |
| Manchester City FC v Southampton FC 15/09/1999 | £12.50 | |
| Chelsea FC v AC Milan 15/09/1999 | £4.00 | |
| Chelsea FC v AC Milan 15/09/1999 | £5.00 | |
| Chelsea FC v AC Milan 15/09/1999 | £4.00 | |
| Chelsea FC v AC Milan 15/09/1999 | £2.00 | |
| Tottenham Hotspur FC v Zimbru Chisinau 16/09/1999 | £4.00 | |
| Tottenham Hotspur FC v Zimbru Chisinau 16/09/1999 | £5.00 |