| Portsmouth FC v Chelsea FC 13/05/1989 | £4.50 | |
| Wimbledon v Chelsea FC 19/08/1989 | £4.00 | |
| Chelsea FC v Queens Park Rangers FC 22/08/1989 | £3.00 | |
| Charlton Athletic FC v Chelsea FC 29/08/1989 | £4.50 | |
| Chelsea FC v Scarborough FC 19/09/1989 | £3.00 | |
| Chelsea FC v Coventry City FC 23/09/1989 | £3.00 | |
| 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 | |
| Chelsea FC v Millwall FC 04/11/1989 | £3.00 | |
| Chelsea FC v Southampton FC 18/11/1989 | £3.00 | |
| AFC Bournemouth v Chelsea FC 28/11/1989 | £5.50 |