| Chelsea FC v Crewe Alexandra FC 06/01/1990 | £4.00 | |
| Crewe Alexandra FC v Chelsea FC 10/01/1990 | View match | |
| 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 | |
| Ipswich Town FC v Chelsea FC 23/01/1990 | View match | |
| 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 | |
| Chelsea FC v Tottenham Hotspur FC 10/02/1990 | £3.00 | |
| Nottingham Forest FC v Chelsea FC 17/02/1990 | £0.00 |