| Liverpool FC v Hull City FC 21/09/1999 | £2.50 | |
| Sheffield Wednesday FC v Stoke City FC 22/09/1999 | £4.00 | |
| Sheffield Wednesday FC v Stoke City FC 22/09/1999 | £2.50 | |
| Arsenal FC v AIK (Stockholm) 22/09/1999 | £5.00 | |
| Fulham FC v Crewe Alexandra FC 25/09/1999 | £4.00 | |
| AFC Bournemouth v Bury FC 25/09/1999 | £6.50 | |
| Coventry City FC v West Ham United FC 25/09/1999 | £5.00 | |
| Arsenal FC v Watford FC 25/09/1999 | £2.00 | |
| Arsenal FC v Watford FC 25/09/1999 | £3.00 | |
| Ipswich Town FC v Manchester City FC 26/09/1999 | £5.00 | |
| Wimbledon v Tottenham Hotspur FC 26/09/1999 | £5.00 | |
| Chelsea FC v Galatasaray SK 28/09/1999 | £3.00 |