| Liverpool FC v Sheffield Wednesday FC 19/12/1998 | £4.50 | |
| Sheffield Wednesday FC v Leicester City FC 26/12/1998 | £2.50 | |
| Aston Villa FC v Sheffield Wednesday FC 28/12/1998 | View match | |
| Sheffield Wednesday FC v Norwich City FC 03/01/1999 | £2.50 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 09/01/1999 | £4.50 | |
| West Ham United FC v Sheffield Wednesday FC 16/01/1999 | View match | |
| Sheffield Wednesday FC v Stockport County FC 23/01/1999 | £2.00 | |
| Sheffield Wednesday FC v Derby County FC 30/01/1999 | £2.50 | |
| Leicester City FC v Sheffield Wednesday FC 06/02/1999 | View match | |
| Sheffield Wednesday FC v Chelsea FC 13/02/1999 | £3.00 | |
| Blackburn Rovers FC v Sheffield Wednesday FC 20/02/1999 | View match | |
| Sheffield Wednesday FC v Middlesbrough FC 27/02/1999 | View match |