| Bury FC v Cardiff City FC 02/10/1999 | £6.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £4.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £2.50 | |
| Charlton Athletic FC v Birmingham City FC 02/10/1999 | £3.00 | |
| Tottenham Hotspur FC v Leicester City FC 03/10/1999 | £5.50 | |
| Chelsea FC v Manchester United FC 03/10/1999 | £5.50 | |
| Chelsea FC v Manchester United FC 03/10/1999 | £5.00 | |
| West Ham United FC v Arsenal FC 03/10/1999 | £6.00 | |
| Southampton FC v Derby County FC 04/10/1999 | £3.50 | |
| Southampton FC v Derby County FC 04/10/1999 | £2.50 | |
| Queens Park Rangers FC v Tranmere Rovers FC 09/10/1999 | £5.00 | |
| Bury FC v Notts County FC 09/10/1999 | £6.00 |