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Details of Chelsea's 1999-2000 FA Cup campaign. Click on the opponent for match report.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat,11 Dec 99 | 3rd | Hull City | (a) | 6-1 | 10,279 | Poyet 3, Sutton, Di Matteo, Wise |
| Wed, 19 Jan 00 | 4th | Nottingham Forest | (h) | 2-0 | 30,125 | Leboeuf, Wise |
| Sun, 30 Jan 00 | 5th | Leicester City | (h) | 2-1 | 30,141 | Poyet, Weah |
| Sun, 20 Feb 00 | 6th | Gillingham | (h) | 5-0 | 34,205 | Flo, Terry, Weah, Zola (pen), Morris |
| Sun, 09 Apr 00 | SF | Newcastle United | * | 2-1 | 73,876 | Poyet 2 |
| Sat, 20 May 00 | Final | Aston Villa | * | 1-0 | 78,217 | Di Matteo |
* Wembley Stadium