| Chelsea FC v Leeds United FC 22/04/1989 | £6.00 | |
| Shrewsbury Town FC v Chelsea FC 29/04/1989 | £4.50 | |
| Chelsea FC v Stoke City FC 01/05/1989 | £4.50 | |
| Chelsea FC v Bradford City FC 06/05/1989 | £4.50 | |
| Portsmouth FC v Chelsea FC 13/05/1989 | £3.50 | |
| Portsmouth FC v Chelsea FC 13/05/1989 | £3.50 | |
| 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 | |
| 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 |