| Liverpool FC v Bradford City FC 01/11/1999 | View match | |
| Liverpool FC v Derby County FC 06/11/1999 | View match | |
| Sunderland FC v Liverpool FC 20/11/1999 | View match | |
| West Ham United FC v Liverpool FC 27/11/1999 | View match | |
| Liverpool FC v Sheffield Wednesday FC 05/12/1999 | £5.50 | |
| Huddersfield Town FC v Liverpool FC 12/12/1999 | View match | |
| Liverpool FC v Coventry City FC 18/12/1999 | View match | |
| Newcastle United FC v Liverpool FC 26/12/1999 | View match | |
| Liverpool FC v Wimbledon 28/12/1999 | £4.00 | |
| Liverpool FC v Wimbledon 28/12/1999 | £5.00 | |
| Tottenham Hotspur FC v Liverpool FC 03/01/2000 | £5.00 | |
| Liverpool FC v Blackburn Rovers FC 10/01/2000 | View match |