| 3. Round | 11/09/1909 | Aston Villa | - | Chelsea FC | 4:1 | ||||
| 4. Round | 18/09/1909 | Chelsea FC | - | Sheffield United | 2:2 | ||||
| 5. Round | 25/09/1909 | Woolwich Arsenal | - | Chelsea FC | 3:2 | ||||
| 6. Round | 02/10/1909 | Chelsea FC | - | Bolton Wanderers | 3:2 |  |
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| 7. Round | 09/10/1909 | Middlesbrough FC | - | Chelsea FC | 0:1 | |
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| 8. Round | 16/10/1909 | Blackburn Rovers | - | Chelsea FC | 1:0 | ||||
| 20. Round | 27/10/1909 | Chelsea FC | - | Preston North End | 2:0 | ||||
| 10. Round | 30/10/1909 | Sunderland AFC | - | Chelsea FC | 4:0 | ||||
| 15. Round | 04/12/1909 | Chelsea FC | - | Bristol City | 4:1 | |
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| 16. Round | 11/12/1909 | Bury FC | - | Chelsea FC | 4:2 | ||||
| 17. Round | 18/12/1909 | Chelsea FC | - | Tottenham Hotspur | 2:1 | ||||
| 18. Round | 25/12/1909 | Notts County | - | Chelsea FC | 2:1 | ||||
| 1. Round | 27/12/1909 | Chelsea FC | - | Newcastle United | 2:1 | ||||
| 31. Round | 01/01/1910 | Newcastle United | - | Chelsea FC | 1:0 | ||||
| 21. Round | 08/01/1910 | Liverpool FC | - | Chelsea FC | 5:1 | ||||
| 33. Round | 10/01/1910 | Preston North End | - | Chelsea FC | 2:0 | ||||
| 25. Round | 12/02/1910 | Bolton Wanderers | - | Chelsea FC | 5:2 | ||||
| 24. Round | 28/03/1910 | Chelsea FC | - | Woolwich Arsenal | 0:1 |
Wales