| 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 | |
| Wimbledon v Chelsea FC 20/05/1969 | £6.50 | |
| 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 West Ham United FC 20/08/1969 | £3.00 | |
| Chelsea FC v West Ham United FC 20/08/1969 | £3.00 | |
| Southampton FC v Chelsea FC 23/08/1969 | £1.50 | |
| Chelsea FC v Arsenal FC 27/09/1969 | £3.00 | |
| Chelsea FC v West Bromwich Albion FC 18/10/1969 | £1.80 | |
| Chelsea FC v West Bromwich Albion FC 18/10/1969 | £3.00 |