| Chelsea FC v Charlton Athletic FC 21/04/1969 | £15.00 | |
| Charlton Athletic FC v Chelsea FC 25/04/1969 | £39.99 | |
| Liverpool FC v Chelsea FC 09/08/1969 | £5.50 | |
| West Ham United FC v Chelsea FC 11/08/1969 | £6.00 | |
| 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 | £4.00 | |
| Southampton FC v Chelsea FC 23/08/1969 | £1.50 | |
| Chelsea FC v Crystal Palace FC 30/08/1969 | £5.99 | |
| Chelsea FC v Crystal Palace FC 30/08/1969 | £5.99 | |
| Manchester City FC v Chelsea FC 06/09/1969 | £5.50 | |
| Manchester City FC v Chelsea FC 06/09/1969 | £4.00 |