1. Round | 01/09/1908 | Chelsea FC | - | Preston North End | 0:0 | ||||
2. Round | 05/09/1908 | Liverpool FC | - | Chelsea FC | 2:1 | ||||
7. Round | 10/10/1908 | Chelsea FC | - | Sunderland AFC | 2:0 | ||||
8. Round | 17/10/1908 | Chelsea FC | - | The Wednesday FC | 2:2 | ||||
9. Round | 24/10/1908 | Blackburn Rovers | - | Chelsea FC | 2:0 | ||||
10. Round | 31/10/1908 | Chelsea FC | - | Bradford City | 1:1 | ||||
11. Round | 07/11/1908 | Manchester United | - | Chelsea FC | 0:1 | ||||
12. Round | 14/11/1908 | Chelsea FC | - | Everton FC | 3:3 | ||||
13. Round | 21/11/1908 | Leicester Fosse | - | Chelsea FC | 5:2 | ||||
14. Round | 28/11/1908 | Chelsea FC | - | Woolwich Arsenal | 1:2 | ||||
20. Round | 02/01/1909 | Chelsea FC | - | Liverpool FC | 3:0 | ||||
22. Round | 23/01/1909 | Chelsea FC | - | Sheffield United | 1:1 | ||||
23. Round | 30/01/1909 | Aston Villa | - | Chelsea FC | 0:0 | ||||
25. Round | 13/02/1909 | Sunderland AFC | - | Chelsea FC | 1:2 | ||||
27. Round | 27/02/1909 | Chelsea FC | - | Blackburn Rovers | 1:1 | ||||
30. Round | 20/03/1909 | Everton FC | - | Chelsea FC | 3:2 | ||||
21. Round | 31/03/1909 | Bury FC | - | Chelsea FC | 2:1 |