| Wimbledon v Sheffield Wednesday FC 19/09/1998 | £3.00 | |
| Sheffield Wednesday FC v Everton FC 24/10/1998 | £3.00 | |
| Sheffield Wednesday FC v Southampton FC 31/10/1998 | £3.00 | |
| Chelsea FC v Sheffield Wednesday FC 28/11/1998 | £3.50 | |
| Chelsea FC v Sheffield Wednesday FC 28/11/1998 | £3.00 | |
| Chelsea FC v Sheffield Wednesday FC 28/11/1998 | £3.00 | |
| Liverpool FC v Sheffield Wednesday FC 19/12/1998 | £4.50 | |
| Sheffield Wednesday FC v Leicester City FC 26/12/1998 | £2.50 | |
| Sheffield Wednesday FC v Norwich City FC 03/01/1999 | £2.50 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 09/01/1999 | £4.50 | |
| Sheffield Wednesday FC v Stockport County FC 23/01/1999 | £2.00 | |
| Sheffield Wednesday FC v Derby County FC 30/01/1999 | £2.50 |