| 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 | |
| Dorchester Town v Chelsea FC 15/10/1990 | View match | |
| Chelsea FC v Nottingham Forest FC 20/10/1990 | £6.00 | |
| Liverpool FC v Chelsea FC 27/10/1990 | View match | |
| Chelsea FC v Portsmouth FC 31/10/1990 | £3.00 | |
| Chelsea FC v Portsmouth FC 31/10/1990 | £4.00 | |
| Chelsea FC v Aston Villa FC 03/11/1990 | £3.00 |