| Wimbledon v Chelsea FC 19/08/1989 | £4.00 | |
| Chelsea FC v Queens Park Rangers FC 22/08/1989 | £3.00 | |
| Chelsea FC v Sheffield Wednesday FC 26/08/1989 | View match | |
| Charlton Athletic FC v Chelsea FC 29/08/1989 | £4.50 | |
| Chelsea FC v Nottingham Forest FC 09/09/1989 | View match | |
| Tottenham Hotspur FC v Chelsea FC 16/09/1989 | £3.50 | |
| Chelsea FC v Scarborough FC 19/09/1989 | £3.00 | |
| Chelsea FC v Coventry City FC 23/09/1989 | £3.00 | |
| Chelsea FC v Arsenal FC 30/09/1989 | £3.50 | |
| Scarborough FC v Chelsea FC 04/10/1989 | £9.50 | |
| Norwich City FC v Chelsea FC 14/10/1989 | £4.50 | |
| Derby County FC v Chelsea FC 21/10/1989 | £4.50 |