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Details of Chelsea's 1908-09 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 16 Jan, 09 | 1st | Hull City | (a) | 1-1 | 18,100 | Hilsdon |
| Sat, 20 Jan, 09 | 1st | Hull City | (h) | 1-0 | 25,792 | Warren |
| Sat, 06 Feb, 09 | 2nd | Blackburn Rovers | (a) | 1-2 | 31,897 | Hilsdon |