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Details of Chelsea's 1905-06 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 07 Oct, 05 | 1st Qual | 1st Grenadiers | (h) | 6-1 | 5,000 | Moran, Robertson, O'Hara 2, Windbridge 2 |
| Sat, 28 Oct, 05 | 2nd Qual | Southern United | (a) | 1-0 | 7,000 | McDermott |
| Sat, 09 Nov, 05 | 3rd Qual | Crystal Palace | (a) | 1-7 | 3,000 | O'Hara |