| Blackpool FC v Chelsea FC 12/12/1959 | View match | |
| Preston North End FC v Chelsea FC 19/12/1959 | View match | |
| Chelsea FC v Newcastle United FC 26/12/1959 | View match | |
| Newcastle United FC v Chelsea FC 28/12/1959 | View match | |
| Chelsea FC v Leicester City FC 02/01/1960 | View match | |
| Chelsea FC v Bradford Park Avenue 09/01/1960 | View match | |
| Burnley FC v Chelsea FC 16/01/1960 | View match | |
| Chelsea FC v Leeds United FC 23/01/1960 | View match | |
| Chelsea FC v Aston Villa FC 30/01/1960 | View match | |
| West Ham United FC v Chelsea FC 06/02/1960 | View match | |
| Chelsea FC v Fulham FC 13/02/1960 | £6.50 | |
| Chelsea FC v Fulham FC 13/02/1960 | £5.50 |