| Bury FC v AFC Bournemouth 23/10/1999 | £5.00 | |
| Queens Park Rangers FC v Portsmouth FC 23/10/1999 | £5.00 | |
| Sheffield Wednesday FC v Coventry City FC 23/10/1999 | £4.00 | |
| Tottenham Hotspur FC v Manchester United FC 23/10/1999 | £5.00 | |
| Charlton Athletic FC v West Bromwich Albion FC 23/10/1999 | £4.50 | |
| Southampton FC v Liverpool FC 23/10/1999 | £4.50 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £2.50 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £3.00 | |
| Aston Villa FC v Wimbledon 23/10/1999 | £3.00 | |
| West Ham United FC v Sunderland FC 24/10/1999 | £5.00 | |
| Crystal Palace FC v West Bromwich Albion FC 26/10/1999 | £3.00 | |
| Charlton Athletic FC v Tranmere Rovers FC 26/10/1999 | £5.00 |