| Chelsea FC v Portsmouth FC 17/01/1959 | £3.00 | |
| Chelsea FC v Aston Villa FC 24/01/1959 | £3.50 | |
| Chelsea FC v Aston Villa FC 24/01/1959 | £7.50 | |
| Chelsea FC v West Ham United FC 07/02/1959 | £12.99 | |
| Chelsea FC v West Bromwich Albion FC 22/04/1959 | £3.50 | |
| Chelsea FC v Preston North End FC 22/08/1959 | £8.50 | |
| Chelsea FC v Preston North End FC 22/08/1959 | £8.00 | |
| Chelsea FC v Manchester United FC 02/09/1959 | £11.99 | |
| Fulham FC v Chelsea FC 26/09/1959 | £2.92 | |
| Manchester City FC v Chelsea FC 14/11/1959 | £5.00 | |
| Chelsea FC v Sheffield Wednesday FC 05/12/1959 | £4.50 | |
| Chelsea FC v Fulham FC 13/02/1960 | £5.50 |