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Details of Chelsea's 1928-29 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 12 Jan, 29 | 3rd | Everton | (h) | 2-0 | 61,316 | Thompson, Miller |
| Sun, 27 Jan, 29 | 4th | Birmingham City | (h) | 1-0 | 56,953 | Miller |
| Sat, 16 Feb, 29 | 5th | Portsmouth | (h) | 1-1 | 38,474 | Law |
| Wed, 20 Feb, 29 | 5th | Portsmouth | (a) | 0-1 | 31,966 |