| Chelsea FC v Wolverhampton Wanderers FC 27/08/1960 | £8.50 | |
| Leicester City FC v Chelsea FC 31/08/1960 | View match | |
| Bolton Wanderers FC v Chelsea FC 03/09/1960 | View match | |
| Chelsea FC v Blackburn Rovers FC 07/09/1960 | View match | |
| Chelsea FC v West Ham United FC 10/09/1960 | View match | |
| Fulham FC v Chelsea FC 17/09/1960 | View match | |
| Blackburn Rovers FC v Chelsea FC 19/09/1960 | £4.00 | |
| Blackpool FC v Chelsea FC 24/09/1960 | View match | |
| Chelsea FC v Everton FC 01/10/1960 | View match | |
| Guildford City v Chelsea FC 03/10/1960 | View match | |
| Millwall FC v Chelsea FC 10/10/1960 | View match | |
| Birmingham City FC v Chelsea FC 15/10/1960 | View match |