| Coventry City FC v Chelsea FC 02/09/1969 | View match | |
| Manchester City FC v Chelsea FC 06/09/1969 | £4.00 | |
| Manchester City FC v Chelsea FC 06/09/1969 | £5.50 | |
| Chelsea FC v Wolverhampton Wanderers FC 13/09/1969 | View match | |
| Chelsea FC v Burnley FC 17/09/1969 | £5.00 | |
| 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 |