| Chelsea FC v Tottenham Hotspur FC 15/04/1960 | £6.50 | |
| Tottenham Hotspur FC v Chelsea FC 18/04/1960 | £12.99 | |
| 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 | |
| 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 | |
| Arsenal FC v Chelsea FC 12/11/1960 | £6.00 | |
| Chelsea FC v Manchester City FC 19/11/1960 | £10.00 | |
| Chelsea FC v Manchester City FC 19/11/1960 | £5.00 | |
| Chelsea FC v Manchester United FC 24/12/1960 | £7.50 |