| 7. Ronde | 10.10.1908 | Chelsea FC | - | Sunderland AFC | 2:0 | ||||
| 8. Ronde | 17.10.1908 | Chelsea FC | - | The Wednesday FC | 2:2 | ||||
| 15. Ronde | 05.12.1908 | Notts County | - | Chelsea FC | 3:0 | ||||
| 16. Ronde | 12.12.1908 | Chelsea FC | - | Newcastle United | 1:2 | ||||
| 17. Ronde | 19.12.1908 | Bristol City | - | Chelsea FC | 1:0 | ||||
| 33. Ronde | 25.12.1908 | Manchester City | - | Chelsea FC | 1:2 | ||||
| 35. Ronde | 26.12.1908 | Chelsea FC | - | Manchester City | 1:2 | ||||
| 18. Ronde | 01.01.1909 | Middlesbrough FC | - | Chelsea FC | 1:4 | ||||
| 20. Ronde | 02.01.1909 | Chelsea FC | - | Liverpool FC | 3:0 | ||||
| 23. Ronde | 30.01.1909 | Aston Villa | - | Chelsea FC | 0:0 |
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