| Chelsea FC v Derby County FC 25/08/1990 | £3.00 | |
| Crystal Palace FC v Chelsea FC 28/08/1990 | £3.50 | |
| Queens Park Rangers FC v Chelsea FC 01/09/1990 | £3.50 | |
| Chelsea FC v Sunderland FC 08/09/1990 | View match | |
| Arsenal FC v Chelsea FC 15/09/1990 | £4.50 | |
| Arsenal FC v Chelsea FC 15/09/1990 | £4.50 | |
| St Pauls v Chelsea FC 17/09/1990 | View match | |
| Chelsea FC v Manchester City FC 22/09/1990 | £3.00 | |
| Walsall FC v Chelsea FC 26/09/1990 | £4.50 | |
| Chelsea FC v Sheffield United FC 29/09/1990 | £3.00 | |
| Southampton FC v Chelsea FC 06/10/1990 | £4.50 | |
| Chelsea FC v Walsall FC 10/10/1990 | £3.00 |