| Chelsea FC v West Bromwich Albion FC 22/04/1959 | £3.50 | |
| Chelsea FC v Ville De Belgrade 29/04/1959 | £28.99 | |
| Chelsea FC v Preston North End FC 22/08/1959 | £4.50 | |
| 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 | £8.00 | |
| Chelsea FC v Birmingham City FC 16/09/1959 | £6.00 | |
| Fulham FC v Chelsea FC 26/09/1959 | £2.92 | |
| Chelsea FC v Sheffield Wednesday FC 05/12/1959 | £4.50 | |
| Chelsea FC v Fulham FC 13/02/1960 | £5.50 | |
| Chelsea FC v Fulham FC 13/02/1960 | £6.50 | |
| Blackburn Rovers FC v Chelsea FC 30/03/1960 | £8.50 |