| 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 | £2.00 | |
| Chelsea FC v Preston North End FC 03/02/1969 | £3.00 | |
| Chelsea FC v Stoke City FC 12/02/1969 | £3.00 | |
| Chelsea FC v Sunderland FC 22/02/1969 | £4.50 | |
| Chelsea FC v Sunderland FC 22/02/1969 | £3.00 | |
| Chelsea FC v West Bromwich Albion FC 01/03/1969 | £4.50 | |
| Chelsea FC v Manchester United FC 15/03/1969 | £4.50 | |
| Chelsea FC v Newcastle United FC 04/04/1969 | £4.50 | |
| Chelsea FC v Burnley FC 05/04/1969 | £3.00 | |
| Chelsea FC v Burnley FC 05/04/1969 | £4.50 |