BACKGROUND: Chondroid syringoma, a tumor of the eccrine glands, suns previously called mixed tumor of skin as it has both mesenchymal and epithelial elements. Malignancy in this tumor is extremely rare. Although there are a few reports describing the cytomorphologic features of chondroid syringoma, the cytologic findings of its malignant counterpart have not been described. CASE: A 40-year-old female presented with a recurrent swelling on the scalp of one year's duration. Fine needle aspiration yielded blood mixed gelatinous material. May-Grunwald-Giemsa-stained smears showed epithelial cells arranged in cordlike structures and ill-formed glands against a myxomatous background. The epithelial cells had scanty cytoplasm and markedly pleomorphic nuclei with prominent nucleoli. A few cells in the stroma had It halo around them and a resemblance to cartilage cells. A preoperative diagnosis of malignant chondroid syringoma was made. The turner was excised, and the cytologic diagnosis was confirmed on histopathology. CONCLUSION: Cytomorphologic features of a rare case of malignant chondroid syringoma are reported for the first rime. The presence of malignant epithelial cells against a myxoid background with a few chondroid foci helped in making a correct preoperative diagnosis.