5. Round | 25/09/1909 | Woolwich Arsenal | - | Chelsea FC | 3:2 | ||||
6. Round | 02/10/1909 | Chelsea FC | - | Bolton Wanderers | 3:2 | ||||
7. Round | 09/10/1909 | Middlesbrough FC | - | Chelsea FC | 0:1 | ||||
20. Round | 27/10/1909 | Chelsea FC | - | Preston North End | 2:0 | ||||
10. Round | 30/10/1909 | Sunderland AFC | - | Chelsea FC | 4:0 | ||||
11. Round | 06/11/1909 | Chelsea FC | - | Everton FC | 0:1 |