| West Ham United FC v Sheffield Wednesday FC 21/11/1999 | View match | |
| Bolton Wanderers FC v Sheffield Wednesday FC 30/11/1999 | £3.50 | |
| Liverpool FC v Sheffield Wednesday FC 05/12/1999 | £5.50 | |
| Sheffield Wednesday FC v Bristol City FC 11/12/1999 | £4.00 | |
| Aston Villa FC v Sheffield Wednesday FC 18/12/1999 | View match | |
| 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 Arsenal FC 03/01/2000 | View match | |
| Sheffield Wednesday FC v Arsenal FC 03/01/2000 | View match | |
| Sheffield Wednesday FC v Wolverhampton Wanderers FC 08/01/2000 | £4.00 | |
| Sheffield Wednesday FC v Bradford City FC 15/01/2000 | £2.50 | |
| Sheffield Wednesday FC v Bradford City FC 15/01/2000 | £4.00 |