| Leeds United FC v Chelsea FC 20/09/1969 | View match | |
| Leeds United FC v Chelsea FC 24/09/1969 | View match | |
| Chelsea FC v Arsenal FC 27/09/1969 | £3.00 | |
| Sunderland FC v Chelsea FC 04/10/1969 | View match | |
| Chelsea FC v Leeds United FC 06/10/1969 | View match | |
| Chelsea FC v Derby County FC 11/10/1969 | View match | |
| Carlisle United FC v Chelsea FC 14/10/1969 | View match | |
| Chelsea FC v West Bromwich Albion FC 18/10/1969 | £3.00 | |
| Chelsea FC v West Bromwich Albion FC 18/10/1969 | £1.80 | |
| Newcastle United FC v Chelsea FC 25/10/1969 | View match | |
| Chelsea FC v Coventry City FC 01/11/1969 | £2.50 | |
| Sheffield Wednesday FC v Chelsea FC 08/11/1969 | View match |