| Chelsea FC v Crewe Alexandra FC 06/01/1990 | £4.00 | |
| 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 | |
| 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 | |
| Crystal Palace FC v Chelsea FC 21/02/1990 | £4.00 | |
| Chelsea FC v Manchester United FC 24/02/1990 | £4.00 | |
| Southampton FC v Chelsea FC 03/03/1990 | £3.50 |