| Newcastle United FC v Sheffield Wednesday FC 19/09/1999 | View match | |
| Sheffield Wednesday FC v Stoke City FC 22/09/1999 | £2.50 | |
| Sheffield Wednesday FC v Stoke City FC 22/09/1999 | £4.00 | |
| Sunderland FC v Sheffield Wednesday FC 25/09/1999 | View match | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £4.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £2.50 | |
| Sheffield Wednesday FC v Nottingham Forest FC 13/10/1999 | £1.50 | |
| Leeds United FC v Sheffield Wednesday FC 16/10/1999 | View match | |
| Sheffield Wednesday FC v Coventry City FC 23/10/1999 | £4.00 | |
| Leicester City FC v Sheffield Wednesday FC 30/10/1999 | View match | |
| Sheffield Wednesday FC v Watford FC 06/11/1999 | £2.50 | |
| Sheffield Wednesday FC v Watford FC 06/11/1999 | £4.00 |