| 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 | £2.50 | |
| Sheffield Wednesday FC v Stoke City FC 22/09/1999 | £4.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £2.50 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £4.00 | |
| Sheffield Wednesday FC v Nottingham Forest FC 13/10/1999 | £1.50 | |
| 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 | |
| Liverpool FC v Sheffield Wednesday FC 05/12/1999 | £5.50 | |
| Sheffield Wednesday FC v Bristol City FC 11/12/1999 | £4.00 |