| Chelsea FC v Charlton Athletic FC 21/04/1969 | £5.00 | |
| Charlton Athletic FC v Chelsea FC 25/04/1969 | View match | |
| Wimbledon v Chelsea FC 20/05/1969 | ||
| Alemannia Aachen v Chelsea FC 02/08/1969 | View match | |
| Liverpool FC v Chelsea FC 09/08/1969 | £5.50 | |
| West Ham United FC v Chelsea FC 11/08/1969 | £4.50 | |
| Chelsea FC v Ipswich Town FC 16/08/1969 | View match | |
| Chelsea FC v West Ham United FC 20/08/1969 | £3.00 | |
| Southampton FC v Chelsea FC 23/08/1969 | £1.50 | |
| Tottenham Hotspur FC v Chelsea FC 27/08/1969 | View match | |
| Chelsea FC v Crystal Palace FC 30/08/1969 | £5.99 | |
| Chelsea FC v Crystal Palace FC 30/08/1969 | View match |