| Wolverhampton Wanderers FC v Sheffield Wednesday FC 18/01/2000 | View match | |
| Tottenham Hotspur FC v Sheffield Wednesday FC 22/01/2000 | £3.50 | |
| Tottenham Hotspur FC v Sheffield Wednesday FC 22/01/2000 | £4.50 | |
| Gillingham FC v Sheffield Wednesday FC 29/01/2000 | ||
| Sheffield Wednesday FC v Manchester United FC 02/02/2000 | £5.00 | |
| Derby County FC v Sheffield Wednesday FC 05/02/2000 | £4.50 | |
| Sheffield Wednesday FC v Southampton FC 12/02/2000 | £4.00 | |
| Sheffield Wednesday FC v Newcastle United FC 26/02/2000 | £4.00 | |
| Everton FC v Sheffield Wednesday FC 04/03/2000 | View match | |
| Sheffield Wednesday FC v West Ham United FC 11/03/2000 | £4.00 | |
| Watford FC v Sheffield Wednesday FC 18/03/2000 | View match | |
| Middlesbrough FC v Sheffield Wednesday FC 25/03/2000 | View match |