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Details of Chelsea's 1968-69 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 04 Jan, 69 | 3rd | Carlisle United | (h) | 2-0 | 37,322 | Osgood, Tambling |
| Sat, 25 Jan, 69 | 4th | Preston North End | (a) | 0-0 | 31,875 | |
| Mon, 03 Feb, 69 | 4th | Preston North End | (h) | 2-1 | 36,522 | Webb, Cooke |
| Wed, 12 Feb, 69 | 5th | Stoke City | (h) | 3-2 | 39,191 | Osgood 2, Birchenall |
| Sat, 01 Mar, 69 | 6th | West Bromwich Albion | (h) | 1-2 | 52,285 | Webb |