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Details of Chelsea's 1965-66 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 22 Jan, 66 | 3rd | Liverpool | (a) | 2-1 | 54,097 | Osgood, Tambling |
| Sat, 12 Feb, 66 | 4th | Leeds United | (h) | 1-0 | 57,847 | Tambling |
| Sat, 05 Mar, 66 | 5th | Shrewsbury Town | (h) | 3-2 | 51,144 | Bridges 2, Graham |
| Sat, 26 Mar, 66 | 6th | Hull City | (h) | 2-2 | 46,924 | Graham, Tambling |
| Thu, 31 Mar, 66 | 6th | Hull City | (a) | 3-1 | 45,328 | Graham, Tambling 2 |
| Sat, 23 Apr, 66 | SF | Sheffield Wednesday | * | 0-2 | 61,321 |
* Villa Park