| Chelsea FC v Preston North End FC 22/08/1959 | £8.00 | |
| 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 | |
| Chelsea FC v Fulham FC 13/02/1960 | £6.50 | |
| Blackburn Rovers FC v Chelsea FC 30/03/1960 | £8.50 | |
| Chelsea FC v Manchester City FC 02/04/1960 | £9.50 | |
| Arsenal FC v Chelsea FC 09/04/1960 | £5.50 | |
| Chelsea FC v Wolverhampton Wanderers FC 30/04/1960 | £7.00 | |
| Chelsea FC v Wolverhampton Wanderers FC 30/04/1960 | £9.00 | |
| Chelsea FC v Leicester City FC 24/08/1960 | £12.50 |