| West Ham United FC v Chelsea FC 12/04/1969 | £5.50 | |
| West Ham United FC v Chelsea FC 12/04/1969 | £4.00 | |
| Chelsea FC v Arsenal FC 14/04/1969 | £4.00 | |
| Chelsea FC v Arsenal FC 14/04/1969 | £5.50 | |
| Chelsea FC v Queens Park Rangers FC 19/04/1969 | £4.50 | |
| Chelsea FC v Charlton Athletic FC 21/04/1969 | £15.00 | |
| Chelsea FC v Charlton Athletic FC 21/04/1969 | £21.99 | |
| 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 |