| Dover Athletic FC v Chelsea FC 02/10/1961 | View match | |
| Sheffield Wednesday FC v Chelsea FC 07/10/1961 | View match | |
| Chelsea FC v Leicester City FC 14/10/1961 | View match | |
| Birmingham City FC v Chelsea FC 21/10/1961 | View match | |
| Chelsea FC v Everton FC 28/10/1961 | View match | |
| Arsenal FC v Chelsea FC 04/11/1961 | View match | |
| Chelsea FC v Bolton Wanderers FC 11/11/1961 | View match | |
| Manchester City FC v Chelsea FC 18/11/1961 | £14.50 | |
| Chelsea FC v West Bromwich Albion FC 25/11/1961 | View match | |
| Ipswich Town FC v Chelsea FC 02/12/1961 | View match | |
| Chelsea FC v Burnley FC 09/12/1961 | View match | |
| Nottingham Forest FC v Chelsea FC 16/12/1961 | View match |