| Chelsea FC v Liverpool FC 18/01/1969 | £4.50 | |
| Preston North End FC v Chelsea FC 25/01/1969 | View match | |
| Chelsea FC v Preston North End FC 29/01/1969 | £6.50 | |
| Chelsea FC v Preston North End FC 29/01/1969 | £7.00 | |
| Southampton FC v Chelsea FC 01/02/1969 | £4.50 | |
| Chelsea FC v Preston North End FC 03/02/1969 | £3.00 | |
| Chelsea FC v Preston North End FC 03/02/1969 | View match | |
| Chelsea FC v Preston North End FC 03/02/1969 | £2.00 | |
| Chelsea FC v Arsenal FC 08/02/1969 | View match | |
| Chelsea FC v Stoke City FC 12/02/1969 | £3.00 | |
| Leeds United FC v Chelsea FC 15/02/1969 | View match | |
| Chelsea FC v Sunderland FC 22/02/1969 | £4.50 |