| Sheffield Wednesday FC v Middlesbrough FC 26/12/1999 | £4.00 | |
| Chelsea FC v Sheffield Wednesday FC 29/12/1999 | £3.00 | |
| Sheffield Wednesday FC v Wolverhampton Wanderers FC 08/01/2000 | £4.00 | |
| Sheffield Wednesday FC v Bradford City FC 15/01/2000 | £4.00 | |
| Sheffield Wednesday FC v Bradford City FC 15/01/2000 | £2.50 | |
| Tottenham Hotspur FC v Sheffield Wednesday FC 22/01/2000 | £4.50 | |
| Tottenham Hotspur FC v Sheffield Wednesday FC 22/01/2000 | £3.50 | |
| 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 | |
| Sheffield Wednesday FC v West Ham United FC 11/03/2000 | £4.00 |