| 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 | View match | |
| Chelsea FC v Crystal Palace FC 30/08/1969 | View match | |
| 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 | View match |