| Derby County FC v Chelsea FC 12/12/1998 | £3.50 | |
| Manchester United FC v Chelsea FC 16/12/1998 | £3.50 | |
| Manchester United FC v Chelsea FC 16/12/1998 | £5.00 | |
| Manchester United FC v Chelsea FC 16/12/1998 | £8.50 | |
| Chelsea FC v Tottenham Hotspur FC 19/12/1998 | £4.50 | |
| Chelsea FC v Tottenham Hotspur FC 19/12/1998 | £3.50 | |
| Chelsea FC v Tottenham Hotspur FC 19/12/1998 | £3.00 | |
| 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 | £25.00 | |
| Oldham Athletic FC v Chelsea FC 02/01/1999 | £5.50 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £3.50 |