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Details of Chelsea's 2008-09 FA Cup campaign. Click on opponent for match report.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 03 Jan 09 | 3rd | Southend United | (h) | 1-1 | 41,090 | Kalou |
| Wed, 14 Jan 09 | 3rd | Southend United | (a) | 4-1 | 11,314 | Ballack, Kalou, Anelka, Lampard |
| Sat, 24 Jan 09 | 4th | Ipswich Town | (h) | 3-1 | 41,137 | Ballack 2, Lampard |
| Sat, 14 Feb 09 | 5th | Watford | (a) | 3-1 | 16,851 | Anelka 3 |
| Sat, 07 Mar 09 | 6th | Coventry City | (a) | 2-0 | 31,407 | Drogba, Alex |
| Sat, 18 Apr 09 | SF | Arsenal | * | 2-1 | 88,103 | Malouda, Drogba |
| Sat, 30 May 09 | Final | Everton | * | 2-1 | 89,391 | Drogba, Lampard |
* Wembley Stadium