| Chelsea FC v Nottingham Forest FC 16/04/1960 | View match | |
| Tottenham Hotspur FC v Chelsea FC 18/04/1960 | View match | |
| Bolton Wanderers FC v Chelsea FC 23/04/1960 | View match | |
| Chelsea FC v Wolverhampton Wanderers FC 30/04/1960 | £9.00 | |
| Chelsea FC v Wolverhampton Wanderers FC 30/04/1960 | £7.00 | |
| Edinburgh Select XI v Chelsea FC 06/08/1960 | View match | |
| Chelsea FC v Edinburgh Select XI 06/08/1960 | View match | |
| Aston Villa FC v Chelsea FC 20/08/1960 | View match | |
| 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 | |
| Leicester City FC v Chelsea FC 31/08/1960 | View match |