| Preston North End FC v Chelsea FC 29/10/1960 | View match | |
| Chelsea FC v Newcastle United FC 05/11/1960 | View match | |
| Arsenal FC v Chelsea FC 12/11/1960 | View match | |
| Doncaster Rovers FC v Chelsea FC 16/11/1960 | View match | |
| Chelsea FC v Manchester City FC 19/11/1960 | £9.50 | |
| Chelsea FC v Manchester City FC 19/11/1960 | £5.00 | |
| Nottingham Forest FC v Chelsea FC 26/11/1960 | View match | |
| Chelsea FC v West Bromwich Albion FC 03/12/1960 | View match | |
| Cardiff City FC v Chelsea FC 10/12/1960 | View match | |
| Portsmouth FC v Chelsea FC 14/12/1960 | View match | |
| Chelsea FC v Aston Villa FC 17/12/1960 | View match | |
| Chelsea FC v Manchester United FC 24/12/1960 | View match |