| Chelsea FC v Wimbledon 02/12/1989 | £3.00 | |
| Queens Park Rangers FC v Chelsea FC 09/12/1989 | £3.50 | |
| Chelsea FC v Liverpool FC 16/12/1989 | £5.00 | |
| Chelsea FC v West Ham United FC 22/12/1989 | £3.00 | |
| Luton Town FC v Chelsea FC 30/12/1989 | £3.50 | |
| Sheffield Wednesday FC v Chelsea FC 14/01/1990 | £3.50 | |
| Chelsea FC v Charlton Athletic FC 20/01/1990 | £3.00 | |
| Chelsea FC v Charlton Athletic FC 20/01/1990 | £3.00 | |
| Bristol City FC v Chelsea FC 27/01/1990 | £6.50 | |
| Coventry City FC v Chelsea FC 03/02/1990 | £4.50 | |
| Chelsea FC v Tottenham Hotspur FC 10/02/1990 | £3.00 | |
| Chelsea FC v Tottenham Hotspur FC 10/02/1990 | £3.00 |