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Details of Chelsea's 1920-21 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 08 Jan, 21 | 1st | Reading | (a) | 0-0 | 15,863 | |
| Wed, 12 Jan, 21 | 1st | Reaqding | (h) | 2-2 | 34,586 | Cock, Croal |
| Sun, 16 jan, 21 | 1st | Reading | (h) | 3-1 | 29,450 | Wilding, Ferris, Sharp |
| Sat, 29 Jan, 21 | 2nd | Swindon Town | (a) | 2-0 | 21,261 | Cock 2 |
| Sat, 19 Feb, 21 | 3rd | Plymouth Argyle | (a) | 0-0 | 37,749 | |
| Thu, 24 Feb, 21 | 3rd | Plymouth Argyle | (h) | 0-0 | 59,871 | |
| Mon, 28 Feb, 21 | 3rd | Plymouth Argyle | * | 2-1 | 26,007 | Croal, McNeil |
| Sat, 05 Mar, 21 | 4th | Cardiff City | (a) | 0-1 | 45,000 |
* Ashton Gate, Bristol