| Sheffield Wednesday FC v Liverpool FC 07/08/1999 | View match | |
| Liverpool FC v Watford FC 14/08/1999 | View match | |
| Middlesbrough FC v Liverpool FC 21/08/1999 | View match | |
| Leeds United FC v Liverpool FC 23/08/1999 | View match | |
| Liverpool FC v Arsenal FC 28/08/1999 | View match | |
| Liverpool FC v Manchester United FC 11/09/1999 | View match | |
| Hull City FC v Liverpool FC 14/09/1999 | View match | |
| Leicester City FC v Liverpool FC 18/09/1999 | View match | |
| Liverpool FC v Hull City FC 21/09/1999 | £2.50 | |
| Liverpool FC v Everton FC 27/09/1999 | View match | |
| Aston Villa FC v Liverpool FC 02/10/1999 | View match | |
| Southampton FC v Liverpool FC 13/10/1999 | £6.50 |