| Chelsea FC v Liverpool FC 27/02/1999 | £0.00 | |
| Liverpool FC v Leicester City FC 21/04/1999 | £3.50 | |
| Liverpool FC v Tottenham Hotspur FC 01/05/1999 | £5.00 | |
| Liverpool FC v Tottenham Hotspur FC 01/05/1999 | £4.50 | |
| Liverpool FC v Hull City FC 21/09/1999 | £2.50 | |
| Southampton FC v Liverpool FC 13/10/1999 | £6.50 | |
| Southampton FC v Liverpool FC 23/10/1999 | £4.50 | |
| Liverpool FC v West Ham United FC 27/10/1999 | £4.00 | |
| Liverpool FC v West Ham United FC 27/10/1999 | £4.50 | |
| West Ham United FC v Liverpool FC 27/11/1999 | £5.00 | |
| Liverpool FC v Sheffield Wednesday FC 05/12/1999 | £5.50 | |
| Liverpool FC v Wimbledon 28/12/1999 | £5.00 |