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Details of Chelsea's 1949-50 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat,07 Jan, 50 | 3rd | Brentford | (a) | 1-0 | 38,000 | Bowie |
| Sat, 28 Jan 50 | 4th | Newcastle United | (h) | 3-0 | 64,664 | Billington 2, Campbell |
| Sat, 11 Feb, 50 | 5th | Chesterfield Town | (a) | 1-1 | 27,500 | Bowie |
| Wed, 15 Feb, 50 | 5th | Chesterfield Town | (h) | 3-0 | 59,660 | Bentley 2, Billington |
| Sat, 04 Mar, 50 | 6th | Manchester United | (h) | 2-0 | 70,362 | Bentley, Campbell |
| Sat, 18 Mar, 50 | SF | Arsenal | * | 2-2 | 67,752 | Bentley 2 |
| Wed, 22 Mar, 50 | SF | Arsenal | * | 0-1 | 66,482 |
* White Hart Lane