| 15. Round | 04/12/1909 | Chelsea FC | - | Bristol City | 4:1 | ||||
| 16. Round | 11/12/1909 | Bury FC | - | Chelsea FC | 4:2 |  |
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| 18. Round | 25/12/1909 | Notts County | - | Chelsea FC | 2:1 | ||||
| 33. Round | 10/01/1910 | Preston North End | - | Chelsea FC | 2:0 | ||||
| 26. Round | 19/02/1910 | Chelsea FC | - | Middlesbrough FC | 2:1 |
England