| Chelsea FC v Stoke City FC 08/10/1927 | View match | |
| Southampton FC v Chelsea FC 15/10/1927 | View match | |
| Chelsea FC v Hull City FC 22/10/1927 | View match | |
| Preston North End FC v Chelsea FC 29/10/1927 | View match | |
| Chelsea FC v Swansea Town 05/11/1927 | View match | |
| Manchester City FC v Chelsea FC 12/11/1927 | View match | |
| Chelsea FC v Nottingham Forest FC 19/11/1927 | View match | |
| Port Vale FC v Chelsea FC 26/11/1927 | View match | |
| Chelsea FC v South Shields AFC 03/12/1927 | View match | |
| Leeds United FC v Chelsea FC 10/12/1927 | View match | |
| Chelsea FC v Wolverhampton Wanderers FC 17/12/1927 | View match | |
| Barnsley FC v Chelsea FC 24/12/1927 | View match |