| 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 | |
| Sheffield Wednesday FC v Chelsea FC 13/02/1999 | £3.00 | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £3.50 | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £2.50 | |
| Nottingham Forest FC v Sheffield Wednesday FC 01/05/1999 | £3.50 | |
| Charlton Athletic FC v Sheffield Wednesday FC 16/05/1999 | £3.00 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £6.50 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £4.00 | |
| Sheffield Wednesday FC v Derby County FC 25/08/1999 | £4.00 | |
| Southampton FC v Sheffield Wednesday FC 28/08/1999 | £3.50 |