| Chelsea FC v Middlesbrough FC 25/03/1990 | £8.50 | |
| Chelsea FC v Derby County FC 31/03/1990 | £3.00 | |
| Chelsea FC v Luton Town FC 07/04/1990 | £3.00 | |
| Aston Villa FC v Chelsea FC 14/04/1990 | £3.50 | |
| Aston Villa FC v Chelsea FC 14/04/1990 | £4.50 | |
| Chelsea FC v Crystal Palace FC 16/04/1990 | £1.00 | |
| Liverpool FC v Chelsea FC 21/04/1990 | £6.50 | |
| Chelsea FC v Everton FC 28/04/1990 | £3.00 | |
| Millwall FC v Chelsea FC 05/05/1990 | £3.50 | |
| Southend United FC v Chelsea FC 05/05/1990 | View match | |
| Fulham FC v Chelsea FC 09/05/1990 | View match | |
| Queens Park Rangers FC v Chelsea FC 11/05/1990 | View match |