| Crewe Alexandra FC v Sheffield United FC 30/01/1999 | View match | |
| Sheffield United FC v West Bromwich Albion FC 06/02/1999 | View match | |
| Arsenal FC v Sheffield United FC 13/02/1999 | £4.00 | |
| Sheffield United FC v Bradford City FC 19/02/1999 | View match | |
| Arsenal FC v Sheffield United FC 23/02/1999 | £3.00 | |
| Arsenal FC v Sheffield United FC 23/02/1999 | £4.00 | |
| Norwich City FC v Sheffield United FC 27/02/1999 | View match | |
| Sheffield United FC v Crystal Palace FC 02/03/1999 | View match | |
| Sheffield United FC v Watford FC 06/03/1999 | View match | |
| Portsmouth FC v Sheffield United FC 09/03/1999 | View match | |
| Tranmere Rovers FC v Sheffield United FC 13/03/1999 | View match | |
| Sheffield United FC v Port Vale FC 20/03/1999 | View match |