| Sheffield Wednesday FC v Liverpool FC 08/05/1999 | View match | |
| Charlton Athletic FC v Sheffield Wednesday FC 16/05/1999 | £3.00 | |
| Sheffield Wednesday FC v Liverpool FC 07/08/1999 | View match | |
| Manchester United FC v Sheffield Wednesday FC 11/08/1999 | View match | |
| Bradford City FC v Sheffield Wednesday FC 14/08/1999 | View match | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £4.00 | |
| 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 | |
| Stoke City FC v Sheffield Wednesday FC 14/09/1999 | View match | |
| Newcastle United FC v Sheffield Wednesday FC 19/09/1999 | View match |