| Chelsea FC v Carlisle United FC 04/01/1969 | £3.50 | |
| Chelsea FC v Carlisle United FC 04/01/1969 | £4.50 | |
| Manchester City FC v Chelsea FC 11/01/1969 | £5.50 | |
| Manchester City FC v Chelsea FC 11/01/1969 | £5.00 | |
| Chelsea FC v Liverpool FC 18/01/1969 | £4.60 | |
| 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 | |
| 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 | £2.00 | |
| Chelsea FC v Arsenal FC 08/02/1969 | View match |