| 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 | |
| Arsenal FC v Chelsea FC 09/04/1960 | £5.50 | |
| Chelsea FC v Wolverhampton Wanderers FC 30/04/1960 | £9.00 | |
| Chelsea FC v Wolverhampton Wanderers FC 30/04/1960 | £7.00 | |
| Chelsea FC v Leicester City FC 24/08/1960 | £12.50 | |
| Chelsea FC v Wolverhampton Wanderers FC 27/08/1960 | £5.50 | |
| Chelsea FC v Wolverhampton Wanderers FC 27/08/1960 | £8.50 | |
| Blackburn Rovers FC v Chelsea FC 19/09/1960 | £4.00 | |
| Chelsea FC v Manchester City FC 19/11/1960 | £9.50 |