| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £6.50 | |
| Sheffield Wednesday FC v Derby County FC 25/08/1999 | £4.00 | |
| Southampton FC v Sheffield Wednesday FC 28/08/1999 | £3.50 | |
| Sheffield Wednesday FC v Everton FC 11/09/1999 | £9.50 | |
| Sheffield Wednesday FC v Stoke City FC 22/09/1999 | £4.00 | |
| Sheffield Wednesday FC v Stoke City FC 22/09/1999 | £2.50 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £4.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £2.50 | |
| Sheffield Wednesday FC v Coventry City FC 23/10/1999 | £4.00 | |
| Sheffield Wednesday FC v Watford FC 06/11/1999 | £2.50 | |
| Sheffield Wednesday FC v Watford FC 06/11/1999 | £4.00 | |
| West Ham United FC v Sheffield Wednesday FC 21/11/1999 | £5.00 |