| Dorchester Town v Chelsea FC 15/10/1990 | View match | |
| Chelsea FC v Nottingham Forest FC 20/10/1990 | View match | |
| Liverpool FC v Chelsea FC 27/10/1990 | View match | |
| Chelsea FC v Portsmouth FC 31/10/1990 | £3.00 | |
| Chelsea FC v Aston Villa FC 03/11/1990 | £3.00 | |
| Portsmouth FC v Chelsea FC 06/11/1990 | View match | |
| Chelsea FC v Norwich City FC 10/11/1990 | £3.00 | |
| Chelsea FC v Norwich City FC 10/11/1990 | £4.00 | |
| Wimbledon v Chelsea FC 17/11/1990 | View match | |
| Manchester United FC v Chelsea FC 25/11/1990 | £5.50 | |
| Oxford United FC v Chelsea FC 28/11/1990 | £5.50 | |
| Chelsea FC v Tottenham Hotspur FC 01/12/1990 | £4.00 |