| Sheffield Wednesday FC v Wimbledon 03/03/1999 | View match | |
| Arsenal FC v Sheffield Wednesday FC 09/03/1999 | View match | |
| Arsenal FC v Sheffield Wednesday FC 09/03/1999 | View match | |
| Sheffield Wednesday FC v Leeds United FC 13/03/1999 | View match | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £2.50 | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £3.50 | |
| Sheffield Wednesday FC v Coventry City FC 03/04/1999 | View match | |
| Everton FC v Sheffield Wednesday FC 05/04/1999 | View match | |
| Manchester United FC v Sheffield Wednesday FC 17/04/1999 | View match | |
| Sheffield Wednesday FC v Newcastle United FC 21/04/1999 | View match | |
| Sheffield Wednesday FC v Chelsea FC 25/04/1999 | View match | |
| Nottingham Forest FC v Sheffield Wednesday FC 01/05/1999 | £3.50 |