| Chelsea FC v Tottenham Hotspur FC 19/12/1998 | £3.50 | |
| Southampton FC v Chelsea FC 26/12/1998 | £4.50 | |
| Southampton FC v Chelsea FC 26/12/1998 | £1.50 | |
| Chelsea FC v Manchester United FC 29/12/1998 | £12.00 | |
| Chelsea FC v Manchester United FC 29/12/1998 | £18.00 | |
| Oldham Athletic FC v Chelsea FC 02/01/1999 | £5.50 | |
| Newcastle United FC v Chelsea FC 09/01/1999 | View match | |
| Chelsea FC v Coventry City FC 16/01/1999 | £3.50 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £1.00 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £3.50 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £4.00 | |
| Oxford United FC v Chelsea FC 25/01/1999 | View match |